“Mom, can you just stop?!”

I hear this about once every two days as I unskillfully parent my two teenagers.

What’s worse? Hearing it from my son is actually a win.

I see him so rarely, the few words he shares, no matter the meaning, feel like the first drops of rain on a dry, hot day.

Last month, instead of continuing to trial-and-error my way through these last years before they fly the nest, I finally decided to educate myself.

I belatedly followed a good friend’s recommendation and read Dr. Lisa Damour’s book “The Emotional Lives of Teenagers: Raising Connected, Capable, and Compassionate Adolescents.” It was eye-opening.

I realized the psychology of teenagers mimics much of what I experienced as an employee and leader of organizations undergoing fast-paced, significant change.

I’m not a psychologist or therapist, nor do I want to equate your teenage children with your employees, but I couldn’t help but see the similarities between the transformation of a teenager and what people experience in an organization undergoing change.

I wish I had known this earlier in my career.

How adults in a changing organization are similar to teenagers

Dr. Darmour describes the teenage years as a time of tremendous change. Hormones, body growth, and massive brain changes. They’re incredibly difficult to experience, and even harder to make sense of.

When my kids dismiss me or look as if their arms are not coordinated with their legs, I remind myself that it’s because of all that change. Their bodies are growing so fast, it’s not all in sync. It’s also their first time experiencing it; they don’t have a manual to follow and guide them through it.

It’s honestly very similar in organizations.

When an organization undergoes change, many of its people do, too. They are trying not only to make sense of the broader changes but also of what they mean for them individually.

In many ways, the employees are reconstructing their sense of identity in the workplace, not dissimilar to how a teenager grows into an adult, figuring out how to use their longer limbs and making sense of their new mental abilities. (Dr. Damour notes that by the end of adolescence, around age 24, an individual’s brain has been “overhauled and upgraded,” and is “faster, more powerful, and more efficient than before.")

Any leader who has guided an organization through change (restructuring functions and roles, implementing new systems and processes, or merging and divesting) knows the tremendous upheaval it causes for people — emotionally, cognitively, and practically in their day-to-day.

The “mom, please stop” process of separation-individuation is critical to adolescents developing their own sense of identity. People whose roles or daily activities are changing have to do the same. Unsurprisingly, even though they are already adults, the change can make them irritable and prone to behaviors that are hard to understand.

What I wish I had known earlier

The entire book is worth a read. Dr. Damour writes in a non-jargony, highly relatable fashion. Her stories bring every concept to life. I can’t do them justice, and I won’t regurgitate her work.

Instead, I’ll highlight the concepts that felt most immediately useful and compelling for me, and that I wish I had known as a leader.

Externalization: It’s not about you

I had never heard this term before, but the visual is very illuminating: it’s when a person comes by and literally “dumps” their burdens on you — their complaints, their worries, their frustrations, their sadness.

It’s hard to tell what they're doing when it’s happening. As an empath, I often get completely consumed by the other person’s emotions. It can be helpful at times, but too often, it’s a distraction that I’m not even aware of. And even if you’re not an empath, you can be completely derailed by what someone shares.

For teenagers, this is often a strategy to offload their struggles. By sharing them with you, they are freeing themselves of the weight.

The same can happen at work. Importantly, you need to be careful that you don’t take on the burden unless it’s actually something you should be responsible for handling. I’m not saying you abandon the “see something, say something” motto. Or you stop supporting your team when they need you.

You just need to be careful about being swept away by someone else’s emotions without first understanding why they are sharing with you.

Not every conversation is a cry for help

In the same vein as externalization, high-agency people too often jump right to problem-solving. I know because I’m one of them.

For teenagers, as they are finding their own agency, they don’t always want or need us to jump in. They are sharing to connect.

Adults in the workplace do this, too. Before you jump in to offer advice or direction, check in with the person to find out what type of support they are hoping for.

Sometimes, they just need a listening ear. As a leader, this can be a relief. You can sit back and simply be present to what they are sharing. In fact, the act of listening actively might be the greatest gift you can give an employee or colleague. We often talk about the desire to be seen and heard. This is that moment.

And if you’re a leader committed to your team’s development, it’s essential that you resist the urge to jump in and instead pause to assess the strategic next step. You will never develop the next generation of leaders if you don’t let them lead (and occasionally, stumble).

Your job is not to make your employees happy

Of all the concepts, this was the one I wish someone had told me years ago the most.

When I was a high school student, I was known for being relentless and overly demanding. One of my nicknames was “warden.” I won’t even name the others.

As I rose in my professional career, I overcorrected. I wanted to be the empathetic leader who prioritized people and their needs above all else. That was neither a sustainable target nor the right one.

I went from demanding work at all hours of the day, 7 days a week, to letting my team off the hook for missed outcomes and contorting myself and others unsustainably to accommodate team members who were not pulling their weight.

A leader needs to balance the needs of individuals with the needs of the organization. There’s no one-size-fits-all approach. It’s a constant recalibration. Anyone who tells you otherwise either hasn’t been a leader or is lying.

The challenge is gauging what your team needs. One of the markers I chose was happiness. I thought that if I could ensure employee happiness, I could retain top talent and accelerate business growth.

But the problem with happiness as a KPI is that you can’t control how someone will react. Happiness is driven by so many factors, many of which the company and the leader don’t control. Trying to hit it, I became distracted by every shift in employee temperament and lost focus on my strategic priorities for the business.

Dr. Damour’s guidance about teenagers was illuminating. Instead of assessing their emotional health through a lens of happiness and comfort, view it through the lens of whether they can self-regulate their emotions.

What that means is that if something highly disappointing happens, it’s actually a good sign that the adolescent feels upset and may even feel upset for some time. The key is whether their reaction feels in keeping with the scale of what happened and the impact it has on them.

Translated into the workplace, leaders would do well not to spend too much time overcompensating for decisions or situations that might leave employees feeling discouraged, irritated, or worse. Instead of trying to mitigate how they might feel, which you can’t control, it’s far more effective to focus on setting them up for success going forward.

For example, if you’ve made a difficult downsizing decision, it’s not helpful to dwell on the disappointment and fear your team might feel as a result. You can be empathetic in your tone, but nothing you do will change the impact of your decisions. Worrying about your team’s reaction, something I used to do, is usually time wasted. Instead, make sure you give them the information they need going forward: updated goals, helpful context, and any operational changes to their work.

People need to be able to express themselves productively

In contrast to overindexing on employee happiness, a far more productive goal is to create an environment where people feel their voices matter and that they have the skills to communicate effectively.

It parallels perfectly what Dr. Damour shares: one of the healthiest goals as a parent is to create an environment where your teens feel they can speak up and be heard.

Employees need this more than ever at work. And leaders need it too. The cost of silence is missed ideas, lowered trust, and increased stress.

You don’t want employees to bottle up their reactions or gossip about them. The key is to help your team understand how to communicate their thoughts effectively. This can be accomplished through establishing norms, training everyone on approaches that work, and then modeling these behaviors.

Importantly, you also need to give your team the room to miss the mark. When you combine teaching with practice (and the space to make mistakes), you’ve created a workplace where people become skilled at navigating difficult conversations, sharing their thoughts, and listening well.

Organizations that invest in these practices will be talent magnets, innovate with agility, and energize their people rather than drain them. It’s what I sought to create in every organization I led, and it’s the goal my clients aspire to today. And it’s possible if you take the time to understand what creates the conditions for a healthy, resilient team.

Your turn

Dr. Damour gave me so much more confidence in navigating this period with my kids. We only have a few more years together. I want to make them count, and I want them to leave with positive memories of how I showed up and not negative ones of how I fumbled our interactions.

Her guidance has become part of my playbook as I coach executives leading through tremendous workplace change. For that, I’m deeply grateful.

What's the concept you wish someone had handed you earlier — in leadership, or in life? I'd love to hear it in the comments.

Leave a comment

SAVE-THE-DATE

Substack LIVE: “Mattering” for the DEI-Allergic

April 27th, 3pm ET / 9pm CET

I’ll be joined by , a veteran DEI leader and expert. He’s the founder & Inclusion Strategist of Inclusion Wins and author of Reconstructing Inclusion on Substack. He’s an instructor, a keynoter, and an all-around incredible leader in the world of real DEI. Join us to learn more about what I mean.

🙏 Thank you for being a part of the Lead without Limits community.

If you found this post useful, I’d really appreciate it if you could give it a ❤️ or share it with another leader who you think could benefit.

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The more we create conversation around the hard topics in leadership, the greater the opportunity we all have to create stronger organizations and more leaders equipped to lead well.

May you lead without limits,

Steve was the guest of honor.

If you don’t know him (and I confess, I didn’t), Steve is a four-man bobsled gold medalist from the 2010 Vancouver Winter Olympics and Olympic Hall of Famer. He’s also the co-founder and former CEO of Classroom Champions (which has served over 5 million students across North America), a board member, and today, is an executive coach working with CEOs and their teams.

When we were introduced, I remember looking up — and up.

6’2”. Former Olympian. Clearly fit. And me, 5’ 3” with plenty of gumption but not an athletic bone in my body, wondering what point of connection we could possibly have.

I did what I tell all my clients to do — be warm, be curious, and be bold. Instead of slipping into silence and darting away, I started peppering him with questions.

One conversation led to another. I didn’t expect how open he would be. How honest. How much he was willing to share about what winning actually costs — and what it costs you when the winning stops.

I was thrilled when he agreed to do a Substack Live together last week. What came out of that conversation is wisdom and guidance that all leaders need, especially now.

Transforming ambition into mental strength: goal persistence

Most of us think about goals as destinations.
Make VP. Hit the number. Get the gold medal.

Steve thinks about them differently — as a system for mental health.

The organization he founded, Classroom Champions, discovered it by accident. They were running a social-emotional learning program in a Florida school district, teaching kids perseverance and goal-setting.

The end-of-year results came back showing 3x improvement in mental health scores compared to other programs. They never set out to improve mental health, but what they taught was helping kids internalize what it felt like to make progress on something that matters.

Turns out a longitudinal study had demonstrated that people with high levels of goal persistence and positive reappraisal have materially less anxiety and depression.

The problem? In sports, goals are obvious. Go faster. Land more shots. But in life and in leadership?

“I want to be a good leader. Okay — what does that mean? And what does that mean to me? And what does that mean to my company and my culture?”

The intricacies are different, Steve shared. These questions led him to become an executive coach, to help leaders make sense of them and not be overtaken by them.

This way of relating to goals was not something I was taught. I’m highly goal-oriented, but I grew up with an all-or-nothing approach. Either go in at all costs or don’t set a target at all for fear of missing it.

It took me years of trial and error and personal reflection to arrive at what Steve’s team teaches at scale: set goals intentionally and build a path towards them that allows for setbacks and pivots, all the while tracking your progress. Through it all, develop the ability to maintain your focus, your motivation, and your commitment to healthy behaviors.

Rather than narrowly viewing goals and the path to them as the end-all be-all, and instead seeing them as a way to build mental fitness. It’s incredibly powerful.

It is how I set goals today, and it’s how I coach my clients, but I didn’t have a name for it. Now I do.

The fuel that gets you there, but then burns you down

And what if you don’t struggle with setting thoughtful goals or with motivation? Maybe the issue isn’t where you are going, but how you do it and what happens when you get there.

Not strong enough. Not fast enough. The team isn’t performing enough. The product isn’t polished enough. This deficiency mindset becomes the engine. It wakes you up. It keeps you moving. It actually works — right up until it doesn’t.

“Then when you actually do the thing,” Steve said, “you never practiced good enough. You never practiced satisfied. And just like anything else in life — if you don’t practice it, how in the world are you going to be good at it?”

The gold medal comes. The IPO closes. The promotion happens. And the person who got you there, the one who ran on jet fuel their whole career, has never once practiced what it feels like to be done.

So they aren’t able to navigate the “done state”.

I recognized myself in this. I’ve been one of those people. The early years of my career: nothing at work was enough. Not what I planned. Not what the team gave. Not what I built. And the cost of that fuel? I didn’t even know I was paying it until the tank ran dry again and again.

If I’m honest, I still struggle with this at times.

If I am tired or feeling overwhelmed, my inner judge takes over, and instead of letting me rest, I feel propelled forward. Sometimes it masquerades as excitement and drive, but when it starts to affect my health (sleep, nutrition, exercise, meditation time), I know it’s a sign to recalibrate.

Hearing Steve talk about this reiterated for me how important it is to stay present to what is happening for me. And to start asking the question: “what’s fueling me this moment?”

If it’s jet fuel, it might be time to stop.

Delusional forgiveness and the art of moving forward

I have to recalibrate a lot. It’s humbling to admit it. But it’s the truth. I’m still learning how to practice good enough.

Steve developed a concept to help him. It came after a difficult period of depression, nine years after winning gold.

Acknowledge it. Learn from it. Move. That’s it.

I always go back to the example of how we celebrate toddlers who stumble, fall, and pick themselves back up as they learn how to walk and run. Somewhere along the way to adulthood, we get it stuck in our heads that it isn’t OK to make mistakes. And yet mistakes are essential to both the learning process and to achieving success.

When we demand perfection, we set ourselves up to procrastinate, be difficult to collaborate with, and feel downtrodden and disappointed when we inevitably miss the mark on our way to finding the answer.

This happened to me in my last job. When I became overwhelmed, I became hypervigilant. I wanted details on everything and asked for 3x as much work on every project as was actually necessary. I drove myself and my entire team crazy. Overthinking and overwhelm became my new normal.

Only when I paused and began to assess which work was actually high risk and couldn’t afford to fail did I realize that most of the work just needed to move forward, even if there would be missteps. Those were just part of the learning process.

Put more simply, delusional forgiveness is just another form of unconditional love. The ability to value yourself as worthy just as you are.

It’s what I practice now, and it’s how I choose to see the mistakes I've made before. I think it’s what’s allowing me to make this my most creative and energizing season of life and work, even though I’m older, slower, and much more creaky.

A new definition of hope that every team needs

Not a wish. Not a prayer. An operating principle. A choice made repeatedly, even when the circumstances are hard.

Steve contrasted this with James Clear’s Atomic Habits approach. He has great respect for Clear — but pushes back on the idea that systems matter more than goals.

“A journey without a destination is wandering. And if all you have is systems and habits but no goal for those habits to fulfill, you’re going to wind up on a treadmill to nowhere.”

I hadn’t thought about it that way. I agree with Steve. Systems alone won’t get you there. Success with meaning comes only when you have the full equation:

That’s the root of what’s made every moment in my career feel great. Hope is the belief you can make it happen. Reframing hope as a reflection of your thoughtful choices (setting goals well, creating strong systems, taking action) transforms what can sometimes feel like an amorphous platitude into a strategic and essential tool.

In a moment when uncertainty looms larger than ever, with geopolitical changes by the hour and increasing AI pressure (existential and immediate), people need hope in order to move forward. Teams need it more than ever in order to stay coherent and aligned. You can only do that as a leader if you create it for yourself first.

Fireproof, not fixed

The last concept Steve shared is the one I keep returning to.

“The fire is going to come. The question is: how do you help yourself be in a position so that when it comes, you are fireproof.”

For Steve, after his own depression, standing five steps from a light rail in Calgary, making the right choice: fireproofing became a daily commitment.

Exercise. Sleep. Clean eating. Guarding the mental habits that led him toward that edge. His phone is set to black and white most of the day. He reads at night with a red filter so he can process the world without getting hijacked by it.

He has ADHD, compounded by concussions from years of bobsled. He’s buried two teammates who took their own lives. He served on the US Olympic and Paralympic Committee Board during the Larry Nassar gymnastics scandal, sitting in a room where he had formal power, watching it be powerless to stop the abuse.

Those experiences, especially the last one, forced him to hold authority and helplessness at the same time. The dichotomy was impossible to reconcile, and it taught him something profound about what we can and cannot control. It gave him permission to stop burning himself down over what sits outside of his agency and to focus on what he can control.

His framework: goals, awareness, control, decisions. Practice it until it’s automatic. So when the temperature rises, and it will, you already know what to do.

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What I’m taking away

I asked Steve what he sees in the people who make it versus those who don’t, whether in the Olympic arena or the C-suite boardroom.

That’s not a performance principle. That’s a life principle.

And it’s ME Work — the internal operating system that makes everything else downstream possible. When we are clear about our internal motivations and how we make decisions, that’s when we can lead others well.

For me, it’s all about how I juggle the different priorities that drive me forward: my business, my creative pursuits, my family, my community, and my health.

And it’s hard.

Right now, it means going to bed earlier and missing time with my family in the evenings. But I know (and they know) that improving my sleep is how I will show up better for all of us.

The short-term pain of missing a movie night is worth it if I want to show up the next day ready for our morning routine, patient when there’s a hiccup in the schedule, and fully present for more emotionally charged conversations, which happen a lot more when there are two teens in the house.

I loved this conversation with Steve. Much of what he shared was a new framing for what I’ve discovered, honed, and use. But it was also a reminder that if you’re committed to growing and improving, the process is never-ending, and that’s a good thing. It means you’ll always have something to learn and to hone.

If this conversation sparked something for you, I’d love to hear what landed most. Drop it in the comments below.

Leave a comment

And if you want more from Steve, follow him at SteveMessler.substack.com (his newsletter is launching soon) or find him on his website SteveMesler.net

Thanks for joining me this week,

Conversation Timestamp Guide

00:00 — Welcome and introduction Kathy introduces Steve Mesler: Olympic gold medalist, co-founder of Classroom Champions, former CEO, board member, and executive coach.

04:30 — Goal persistence explained Steve defines goal persistence and how Classroom Champions accidentally discovered its link to mental health outcomes through a Florida school district study.

08:00 — Goal clarity as the foundation Why you need goal clarity before you can have goal persistence — and why it’s harder in life than in sport.

09:30 — Framing fear as excitement Steve’s technique for reframing internal states: nervous, afraid, and excited feel identical in the body. You choose what to call it.

11:30 — Steve’s path to bobsled From national champion track athlete to being banned from the University of Florida’s training room — and the couch in Gainesville where a new path began.

15:30 — The Stockdale Paradox and becoming a new person How Steve applied Good to Great’s Stockdale Paradox to decide he was done getting injured — and didn’t miss a single race in 10 years.

18:30 — Jet fuel: the high achiever’s toxic engine The concept of running on “not good enough” and what happens when the achievement finally arrives — and you’ve never practiced satisfaction.

25:00 — After the gold: what happens when the goal is gone Post-pinnacle disorientation — in sport, business, and life. Why people who sell their company are often not happy.

30:00 — Steve’s depression and the moment that changed everything Nine years after winning gold: the weight of buried teammates, the gymnastics scandal, a flat organization, new fatherhood — and the light rail in Calgary.

33:00 — “My brain was broken, just like my hamstring” How Steve found a way to frame depression as an injury — and eventually as a gift.

36:00 — Delusional forgiveness The practice of learning from failure without staying trapped in it — and why it’s essential for forward momentum.

37:30 — Hope as an operating principle Dr. Quintana Adolfo’s definition of hope: “My actions today will make my tomorrow better.” And why Steve believes leaders who can instill this are done with the hard part.

40:00 — Goals vs. systems: pushing back on Atomic Habits Why Steve believes a journey without a destination is just wandering — and what the neuroscience of dopamine and serotonin has to do with it.

42:00 — How to get comfortable spending most of your day uncomfortable Clarity on the goal makes discomfort manageable. Steve’s example: protecting his four-year-old son.

44:30 — The Big Five goals framework Career, wealth, relationships, lifestyle, health — and why the goals you haven’t examined in relationships and health are quietly shaping your work decisions every day.

46:30 — The daughter who calls her dad Steve’s long-term relationship goal with his 8-year-old: being one of her first calls when she gets her heart broken at 25 — and how that goal shapes how he parents today.

47:30 — Leading through layoffs and AI disruption How leaders under board pressure can still foster hope in their teams — and why assumptions about what your people are actually afraid of are almost always wrong.

51:00 — Caring for yourself during restructuring You have to put your own mask on first. Exercise, sleep, nutrition — these aren’t soft. They’re how you make better decisions when the pressure peaks.

56:00 — Fireproof, not fixed The practice of building your system before the crisis hits — so that when the fire comes, you don’t burn down.

01:00:00 — Close: “This too shall pass” Steve’s final word on navigating hard seasons: the high passes and the low passes. What matters is staying clear, staying intentional, and trusting the practice.

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It was his company, his idea, the source of his energy for nearly a decade. But he no longer wanted to be there.

To be honest, he’d known for some time. Maybe more than a year ago.

But there was no succession plan. No one he felt safe enough to confess to. The business was not robust enough. The Board wouldn’t trust anyone else to lead. His fellow leaders would panic if he left.

So he stayed silent, while his apathy slowly seeped into his work.

Decisions that he could have made within hours were now taking days. Issues that had previously felt minor began to grow in scale and complexity. The rhythms and demands of the business started to feel like a ball and chain, dragging him down slowly and steadily each day.

His colleagues, the other leaders on the team, felt something was off, but they rationalized it: it’s just a passing down cycle. He’ll snap out of it.

They did what too many organizations and leaders do, but later wish they hadn’t: They waited.

Is this happening in your organization?

It happened in several of mine. I saw it happen to other leaders as I stood by the sidelines, trying to avoid the issue.

Eventually, it even happened to me. I was the leader who wanted to go, but didn’t know how. I let it drag on for months.

Just as my boss, the CEO, was rationalizing the decision to wait, I was doing the same. I wasn’t sure what I wanted to do next. I didn’t want to be without income — that felt irresponsible. There was always one more meeting, one more project, one more client conversation I couldn't walk away from.

And yet, if I’m really honest, the core of what I was unwilling to confront was shame, guilt, and fear. Shame that maybe I couldn’t cut it. Guilt that I would be leaving my team behind to fend for themselves. And fear of the unknown, and whether it was actually OK to leave.

It’s easy with 20-20 hindsight to be critical. But when you’re in it, it’s a completely different experience.

You either don’t even know it’s happening.

Or you’re so wrapped up trying to avoid the issue, you forget that you have a choice.

You always have a choice.

Losing a leader, especially one with a long tenure, doesn’t just feel scary, it’s downright horrifying.

The reasons aren’t far-fetched. They’re rather logical.

If you’re brave enough to even contemplate the issue, the litany of questions to deter you from taking action is never-ending and impossible to answer:

What will people on the team think?
How will we replace their years of knowledge?
How will customers respond? Will they get spooked?
Could we have done something different to retain them?
Will the rest of the leadership team stick around for who’s next?
What if we can’t find a better replacement?

The uncertainty is too anxiety-inducing to face.
So instead, we avoid it.

We make excuses — Now isn’t the right time. They just need more support.

We justify — They wouldn’t push us out. We need to give them a little longer.

We deny the truth — The risks aren’t that bad. We can’t create a feasible mitigation plan.

We let our fears drive our path forward and let our leadership judgment slip out the back door.

It’s a terrible path, but it often feels like the easier one to take.

What starts easy turns hard… fast.

A leader who no longer wants the job is one of the most dangerous people you can keep on a team.

Even if they don’t want to hurt the company. In fact, the ones who still want to help are the most lethal. The ones who still want to do right but have not yet acknowledged that they no longer want in.

Those are the ones that wreak the most havoc.

Why?

Because what they are doing is insidious, not conscious, and wrapped in the veneer of good intentions.

The ones who are openly difficult, negative, and malicious make it obvious that they are a threat. You might still take too long to remove them, but at least it’s all out in the open.

The ones who are still parroting the mission and goals (but are questioning the strategy), show up looking prepared (but are only going through the motions), take on just enough work (but nothing extra or more risky) — those are the ones to worry about.

They hurt your progress and your team through small, seemingly innocuous acts:

• Confusing the team through small misdirections — “Don’t follow what was said in that last email. They don’t know what they’re talking about.”

• Creating mini-fissures through gossip — “Did you hear what [so-and-so] said after the meeting? I don’t think they are on board, but don’t talk to them about it.”

• Blocking progress with small comments — “I’m not sure why we are bothering. It hasn’t worked in the past.”

They will subtly add doubt to a discussion. They will delay key decisions. They will think smaller. They will focus on risks more than opportunities. They will shift your overall ethos from growth and innovation to steadiness and risk mitigation.

Your team will feel the pain, but won’t necessarily understand where it’s coming from and why. They will just start to feel the organization stagnate or stumble more. Work will become more arduous and progress more elusive.

And the leader who is struggling? They won’t even know they are doing it.

Because they are in denial just as much as you are.

Facing reality: motivation is what unlocks skills and knowledge.

Obligation is not the same as motivation.

That’s what leaders who no longer feel connected to a business confuse. They think their loyalty and commitment can hide their lack of energy for the mission and the work.

But they aren’t interchangeable. And one can’t mask the other.

“Have-to” thinking may yield some short-term results, but it will not unlock someone’s full potential. It will simply burn them out.

Even if a leader is the smartest person in the room and knows where all the bodies are buried, they won’t be powerful or even productive if they are no longer feeling motivated.

I like to think of our skills and knowledge as sitting in a metal canister. They may be valuable, but no one can see them or access them until you open the canister.

The opening only happens when you feel motivation. It comes from within and can’t be manufactured.

Sometimes, you can adjust the conditions to make it easier to create the opening for someone:

• Finding something adjacent and connected that matters to them can be a motivator (e.g. money, or the ability to learn)

• Adjusting the role and responsibilities to make them fit their current lifestyle needs and interests (e.g. going remote, or scoping down or up)

• Adding support structures and systems can make the job easier to navigate (e.g. a chief of staff, a coach, or AI agents)

But sometimes, those adjustments aren’t enough. They just don't feel as connected to the work anymore.

No amount of external work will solve that. And if they can’t see it, it’s your job as a leader to address it.

Because the alternative is too costly. It isn’t just lost time, it’s losing the momentum, the focus, and ultimately, the trust of your team.

Your turn.

Have you ever worked alongside a leader who was ready to go, but didn’t know it? Or maybe you were the leader, and it took you a minute to realize it was time?

I’d love to hear what helped you and the organization transition through that time — and what didn’t. If you’re willing to share, please add a Comment. I’d love to hear from you.

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If this post resonated, or made you pause and consider your own motivation level or that of your fellow leaders, please consider giving it a ❤️ and sharing it with a friend or colleague who would also benefit. Thank you!

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Mark your calendar for my next Substack Live.

This Friday, I’m talking with Olympic Gold Medalist and now a CEO Performance Coach — . Join us as he shares his key learnings from the training room to the board room. (Event Link)

As always, thank you for joining me each week as I dive into what it takes to lead without limits.

A new client scheduled a call to talk about her career.

Three weeks later, on the day of our first session, she was laid off.

Sadly, she’s not alone.

According to layoffs.fyi, as of March 27th, 40,482 tech employees have been laid off across 71 tech companies in 2026. That’s in addition to the 125,000+ in 2025, and 152,000+ in 2025.

And that’s only in Tech.

According to the ADP® Employment Report, while some sectors show gains, like education and health services (+74,000) and small businesses (+30,000), those are offset by losses in professional/business services (-57,000) and large companies (-18,000).

So what’s a senior leader to do?

Is it worth it to stay in corporate, where even if you’re the one rearranging the deck chairs, it still feels like you’re a cog in a system that is not fully in your control?

Is a sabbatical or a fractional role a better route? What about a wholesale change, going back to school, or becoming a solopreneur?

These are the questions I’m hearing from senior leaders.

My overall answer is: all of these paths are valid, and any one could be the right choice for you.

But I’ve noticed a trend. All the job cuts, AI frenzy, geopolitical challenges, and the hype about the creator economy have turned light-weight FOMO into deep anxiety and fear.

Corporate leaders, once confident that they were climbing the right ladder, are now wondering if they chose the wrong jungle gym or playground. They aren’t just worried that they are not on the fastest track; they’re worried they are climbing on top of quicksand. And they’re wondering whether they somehow missed the memo and should be opting out of the corporate track and creating a completely different path.

As one of those corporate leaders who has chosen the solopreneur path and is often posting on social media about my post-corporate journey, I want to dispel some myths (kill a little FOMO) and reinforce why most of my clients are staying on the corporate track, and why I support it.

(Even if you know all of this already, it’s worth seeing it in black and white, written down, before you make your decision on what’s next.)

Money, money, money.

Let’s be honest, this is the number one thing senior leaders worry about.

Private schools, college, vacations, retirement, a mortgage, energy bills, and of course, keeping up with the Joneses. Some of these are valid reasons, some less so, but all of them result in the same issue: you need more money, not less.

And a corporate job fills this need better than any other path.

The reality is that if you’re a senior leader, you’re probably earning at least $200K in cash comp (at a smaller, perhaps private firm), and some of you are earning well beyond $500K. It’s not just the money — the regularity and predictability of it.

Replacing that income through a creator business or side hustle isn’t just hard; it will take years for most people. And even if the annual sums add up, you might have a level of lumpiness that will make you break out in cold sweats every few months.

But this isn’t the full picture of why people stay in corporate roles. The entire list of monetary is much longer, especially if you’re at a big, publicly traded firm — the ones most people love to hate.

Here’s what I personally experienced and what many of my clients grapple with:

• Cash Compensation: It’s the dollars and the predictability.

• Cash Bonus: Less predictable but a great upside.

• Equity: Public companies give you the most liquidity, but the dream pitched by start-ups can feel just as attractive if your stake is large enough.

• Matching 401Ks: Essentially free money that compounds tax-free.

• Healthcare Benefits: Premiums now cost $20-60K+ a year for a family of 4, and it’s only going higher. If your company covers any portion, don’t underestimate that value.

• Food, Travel, Perks: These may not feel like essentials, but they add value, and if the annual trip to the U.S. Open box or the golfing gala is something you enjoy, don’t forget to add that in.

When you tally it up, you might have to add an additional $50-100K or more to your cash compensation to capture the full value of staying in a corporate role.

When I made two significant choices to reduce my income, in both cases, I weighed the above carefully in my mind for several weeks, and if I’m honest, maybe months. These decisions weren’t just about how much I could live with, but about what I was going to be able to provide for my family.

In the end, I resolved that my family and I didn’t need more. In fact, we were going to be just fine living on less. But it was only because I had pursued earning more money earlier in my career and because I knew what mattered more to me than money: more aligned purpose in how I spent my days and more recently, more agency over my time.

Wanting money isn’t being greedy. Choosing how much and aligning that with your values and what matters most to you — that’s the real question.

Status is real.

As a proponent of sourcing your worth from within, this one is a strange one for me to write about. But I’d be lying if I didn’t.

Status is something that most people have valued at one time or another. How much you define your self-worth by it is where most people get into trouble.

Rely on it too much, and you start to make decisions based on other people’s values rather than your own. Ignore it, and you will find it hard to navigate almost any community of people you want to belong to.

But the fact that it matters? Well, unless you are a full-on recluse, it does.

• Brand: When you are associated with a well-known company (with some reasonably positive cache), you are viewed more positively. It’s the power of notoriety and association bias.

• Credibility: Association bias… again. When you work for a larger business with a proven track record, you’re viewed as more talented, smarter, and more successful. You may be all of those things, but this is about how you’re viewed before someone knows you — when you haven’t demonstrated any of it. This is the power of a name-dropping the right corporate name.

• Awareness: A larger organization often translates into a larger platform from which to build your personal brand. The company's reach helps propel your reach. Speaking events, conferences, and industry associations all help you build your notoriety, which can open doors to new opportunities in all aspects of your life.

• Budget: When you hold the purse strings, you hold the power. Vendors want your business, partners want to collaborate, and people orient to your needs. It’s not actually about you; it’s about your role. But it still feels nice to have people mold to you.

• Title: I hate this one, but even I have to admit: words have meaning. Titles should probably mean less than they do, but they convey so much: the years of work, the evidence of accomplishments, the responsibilities bestowed, the acknowledgement from people more powerful than you. You shouldn’t be defined by your title, but it’s also OK that you value it and all it represents.

• Team: When you are the leader and manager of others, your decisions have a broader impact. That’s real. The size of the team you are responsible for can have significant meaning. In addition, there’s followership, whether people want to work with you again enough to “follow” you to your next role. This isn’t just nice; it can mean the difference between struggling to find great talent and bringing them with you everywhere you go.

Appreciating one or all of these status “symbols” doesn’t make you a status-seeking leech. It’s OK to see the value in some or all of them because others see value in them. It means you’re human and that you’re willing to be honest about what actually matters to you.

For your long-term well-being, the more you can source your self-worth from the inside, the less likely you’ll overindex on the importance of these external measures of success.

And if you want to continue to operate successfully in the business world, these aren’t just symbols; they are real assets.

Building community and your network is easier.

Status is one thing, but there is something else that comes with having a group of people around you: community. When you spend nearly 50% of your waking hours with the people you work with, and you can find common ground, relationships naturally form.

Outside of your family, you likely won’t have that much interaction with anyone else (maybe sad, but definitely true). These people become confidantes and friends. They become your support system. Not every job will offer this, but many will. It’s one of the top things retirees miss: the sense of being part of a larger group with a shared purpose.

Even if community isn’t meaningful enough for you (or you haven’t found a friendly one at your organization), you know I am a huge proponent of nurturing your network. Corporate roles make this so much easier.

When people know you, and you know them, there’s more trust. And trust is the only currency of business that truly matters outside of money.

You know this already in your own career. Most senior leaders earn the promotion, get the new job, and learn about an exciting new company all through one source: their network. I landed my last 3 company positions all through connections.

As you progress in your career, your relationships matter in all aspects of your work. They become your pathway to funding, to experts, sourcing talent, and business opportunities. It’s how I built multiple teams — hiring past colleagues — and it’s how I’m building my current business, which is 80% referral-based.

The easiest way to expand your network? Through affiliations.

Alumni and community groups are great, but it’s even easier when you wear the same logo and share the same mission and goals. People actually respond to your outreach. It’s part of your job to get to know others in the organization, which reduces the cringe factor. And larger corporations also host more group events (trainings, celebrations, annual and quarterly meetings) and will send you out to industry events to further build your connections.

Simply put, being in the corporate world makes it easier to broaden your relationships and strengthen your network, an asset that is hard to measure and takes time to build. And yet, when you deploy it, you realize how essential it is to your success and how grateful you are that you have it.

You get to stay in your lane (sort of).

OK — money and connections. That should be more than enough reason to stay in corporate for most people. But there is one more reason worth highlighting on why staying is the better choice for many people: focus.

When you’re a corporate cog with a certain purview assigned to you, it can feel stifling if you want to spread your wings into other domains out of curiosity (I was always wondering what it took to lead in a different function) or frustration (difficult colleagues always inspired my inner land-grabber). But the boundaries of your role definition can also be freeing when it allows you to focus on just one bucket of tasks.

As someone who is now the receptionist, accounts receivable, brand strategist, and legal (to name just a few of the hats I wear), it can be hard to juggle all the different contexts and tasks.

AI, global freelance talent, and the plethora of digital tools available make it easier. But cognitively, you still need to understand the value of each domain enough to determine whether and how you will address it. That takes time and mental load.

Sure, the freedom to choose when and how is wonderful. And if you’re aiming to stay small, many tasks may not matter all that much at all. But, at a minimum, you will need to directly oversee your marketing, sales, product or service delivery, billing, and bookkeeping. It’s not rocket science, and for many (if not most) leaders, it will be a hard transition.

What corporate haters don’t share on social media.

There are many reasons why the corporate world deserves the ire of the masses. And when you read about all euphoric post-corporate journeys of creators, here’s what most won’t share:

• How much is in their bank account: Most have a healthy, if not substantial, financial cushion before they start: Family money, a huge payout from a transaction, the # of years they’ve been earning big and saving more

• How much income they have from other sources: The people making the biggest bets or sustaining the process the longest? They have existing, ongoing sources of income: A spouse or partner, investments throwing off cash, a side business they’ve been cultivating for years, Board seats paying out $100K+ a year + equity

• How much experience they have doing the work and failing at it: They tout their hundreds of thousands of followers or million dollar earnings, but what you don’t often hear is how they were writing for 10 years before they went viral and the several entrepreneurial attempts that failed,

• Profit vs. revenue numbers are often opaque: Yes they might have pulled in several million dollars, which is impressive. But over how many years, and how much did they spend achieving it. You don’t hear about the $100K+ they’ve spent on courses and coaches, the $60K they spend on a social media agency, or even the $40K they spend on the executive assistant. These deflate the story, so they most won’t share it.

• How hard is it to deal with unpredictable revenue streams: The months sweating it out and biting their nails about whether they need to start the job search, the credit card debt they rack up along the way

• How many hours it takes to build: You see them sipping cocktails and traveling the world. But you don’t see the months (or years) of nights and weekends building, testing, and missing the mark. Even with the help of AI, the work is significant. AI accelerates what you know. But most solopreneurs don’t know much when they are formulating their ideas — that’s what takes time.

• Collaborating with the right people at the right time: Referral networks, expert agencies, and other insider tips can transform a business. Learning what these are and finding the “right” people is more art and luck than science and systems.

• They don’t have children or caregiving responsibilities: If you look under the hood, many of these creators (not all) don’t have a family to support or care for, or they didn’t when they started their business. The hours and routines they kept aren’t far more difficult if you have other life responsibilities.

For me personally, I don’t often share that I benefit from years of saving much more than spending, a husband who still has a modest income, and some generational wealth that is both not mindblowing and is more than enough to give me the room to build out my practice at a sustainable pace.

You don’t need to have all of the above to feel financially secure to explore the world outside of corporate work, but if you don’t have at least one or two of these elements, you will face what most do: a reckoning in a year or two that will have you back on the job market.

I don’t say this to be negative. I say it because I’ve seen it. It’s been the case for 90% of the people I’ve met, or of the ones I've dug under the hood to better understand their circumstances. The 10% exists, and that could be you, but those aren’t odds I would personally take, so why would I guide you to do differently?

The kernels of truth worth considering.

There are aspects of the social media content firehouse worth taking the time to reflect on.

The one I guide my clients to, and what helped me most in my career, was: acknowledge who you are today and the season you’re in.

For example, if you’re finding that the deep analytical skills you honed and enjoyed early in your career are no longer as interesting to you and that you’re craving more public speaking and interpersonal development, maybe it’s time for a change.

Or, if you were able to put in long hours when your kids were young, but as they’ve gotten older and you’re now caring for your parents as well, you need more flexible hours and, frankly, less time working, perhaps it's time to dial it back.

I had a long and fulfilling corporate career because I kept acknowledging both what I wanted to delve further into and when I needed to adjust my capacity (sometimes reluctantly), and made the shifts I needed.

I changed roles and industries the way that some people change their clothes. Every 6-12 months, I had a new role. Every 3-5 years, I switched industries. This philosophy allowed me to leave when a role or company was no longer right for me and gave me renewed energy by trying on another role, another company, or another industry.

If you continually take on or stay in roles and work in companies and with people who drain you, no amount of money will cover the cost of your despair and the cost on your health.

Some semi-final thoughts.

I don’t know that I said anything novel or particularly insightful in this post. I wasn’t trying to.

I was simply hoping to help those of you who have felt the heightened sense of anxiety and are spending more time than is useful ruminating about whether you should be staying in the corporate world.

If you find yourself spinning again, try breaking the pattern with one of these DO’s:

If you found this post valuable, you can support my work by sharing it, adding a ❤️ to it, or leaving a Comment.

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I write these posts every week because in this season of life, I’m choosing to only work with a few clients at a time, but I want to support so many more. Your support helps me reach more leaders who might benefit. Thank you!

Want more from me?

If you’re feeling that something needs to shift in your career, here are some past pieces that you might find valuable:

• Make a Plan to Break Free from Your Golden Handcuffs Before It’s Too Late — a counterpoint to this piece.

• Generate Life-Changing Wealth Without the Risks of Entrepreneurship — if you really want to shift from employee to owner, this is a good read.

• The Surprising Way to Reclaim Your Power After a Layoff — for anyone who is navigating the moment after.

• Longing vs Fear: The Real Battle Behind Your Career Crossroads — another way of viewing what

If you want to see all my most popular posts, here’s a shortcut: Career, Leadership, Mindset.

Working with me.

I don’t take on more than a few clients at a time so that I can be laser-focused on their needs. I’m happy to report that a few clients have landed new roles or have found a clear path forward, so I’m opening up a few spots for new clients:

• Individual Leaders - If you’re feeling like the playbook that has worked in the past isn't serving you anymore, but you aren’t sure what’s next, I’m opening up 3 spots for execs who need a true thought partner and someone who’s been in their seat.

• Leadership Teams - If your leadership team is no longer feeling in sync or on track and you’re not sure what is happening or how to shift it back into high gear, I’m helping one new client to go deep: diagnose, coach you and your leaders 1:1, and facilitate group sessions to reset and revamp how you work together.

If this sounds like you or your team, book a free consultation to explore if working together makes sense.

Thank you for reading!

May you lead without limits,

Yesterday morning, my paternal grandmother passed away.

I called her Nai Nai.

She was 101, and after months of fearing what was beyond, she told my father the hour before she passed, she “was going home.”

As I thought about my post this week, it became obvious: I’d share the lessons I learned from my grandmother, both what to emulate and what to avoid.

Her life was nothing notable for most people, and yet, it has always felt extraordinary to me, filled with courageous moves and perseverance almost to a fault.

I’m sad, and I need time to grieve. But grief is a funny business. It shows up differently for everyone. For me, the best way to honor my grandmother and process my feelings is to translate what I learned from her into leadership lessons I value and will continue to carry forward.

But before I share the lessons, let me give you some more context about my grandmother’s life.

From idyllic to turbulent, growing up without guarantees.

My grandmother grew up in China. I think it was in Jiangsu province on the eastern coast. (I wish I had more details, but thank you in advance for not judging.)

Nai Nai grew up in a well-to-do family. They had servants, cooks, and people who took care of my grandmother’s and the family’s needs. My grandmother started life sheltered. But all around her, the world was shifting. It was a time of significant social and political change.

Imperial China was ending. Women were no longer binding their feet, and they were starting to work outside the home. The Nationalists, Communists, and the Japanese were all battling for control. One of the few memories she shared with me was hiding in bomb shelters, and a deep distrust of Japanese people, all fostered in her early life.

As a young adult, she worked for the Nationalist government, and when its leader, Chiang Kai-shek, fled China before the Communists took over, she left, too. Her older sister was a leader in her local Communist Party outpost, and convinced the rest of the family to stay.

So, in a path that would be mirrored in the future, Nai Nai left her family and all her possessions behind and fled to Taipei, Taiwan, uncertain of the future, but convinced she could no longer stay in the home of her ancestors.

When I think about her decision, I can’t imagine what she might have felt. To go against her family and make an independent choice had to be hard, if not impossible. Daughters didn’t do that. And to go to a foreign land, with little to no money, and not know if you will see your family ever again? I know people around the world still grapple with this. And I am so fortunate that I can’t imagine it.

Leaving the workplace to work at home.

In Taipei, my grandmother met my grandfather, my Ye Ye, who also worked in the Nationalist government. The married and had 3 boys; my father is the eldest.

In Chinese culture, at the time, boys were considered princes, never to lift a finger, always to be prized.

Caring for 3 boys and my grandfather would have been a lot. But that wasn’t the family Nai Nai was responsible for.

My grandfather, unlike my grandmother, didn’t come to Taipei alone. He brought his grandmother and was joined later by his elder and younger sister and their families. This meant my grandmother was responsible for caring for all of them — alone.

Nai Nai left the workforce to become a full-time caregiver for a household that grew to 8. She did the daily shopping, prepping, cooking, cleaning, washing, and mending.

The long days of physical toil were brutal. Her hands were washed raw, her body ached daily. Her feet became deformed from wearing dress shoes that warped them as she trekked to complete her chores. She became humpbacked over time, and her spine never recovered.

But none of the physical labor compared to the emotional stress of being treated like a servant by her husband’s family members. It may have been the 1950s, but they held on to cultural norms of the past. The daughter-in-law was there to serve their needs, and they would make sure she did so.

Elite schools and American dreams.

My father and my uncles, with a few challenges, excelled at school. They were the picture of what Chinese families valued. And when it came time to figure out what came after college and their required military service, each left, one by one, for America.

And they never returned, at least not to live.

My grandparents came for a stint to stay with my family during the 1980s. While their time in Texas with us was fine, they could not tolerate the cold when we moved to New Jersey. Coupled with feeling trapped in suburban streets (they missed the city) and a community in which they couldn’t communicate (they couldn’t speak or read much English), they packed up and returned to Taiwan.

We missed them. I was fortunate. I had spent almost every summer of my life with them until elementary school. These were such formative travels that Mandarin felt like my first language, not English, even though I was born in the U.S.

My memories of my grandparents were of doting, caring people who spoiled me and loved me dearly. As I got older, they, along with my Mandarin, faded from my day-to-day life. They became foreign, a hazy concept — people I knew, but not really.

The struggles and peace in the final seasons of life.

I went back a few more times, once in high school and then in adulthood, but my visits were few and far between. Life had gotten full and trips to Asia were costly and time-consuming. I valued my grandparents, but I struggled to make time for them.

In 2002, my Ye Ye passed away from cancer. Nai Nai entered a new season of life. She was alone for nearly two decades, with brief visits from my father and his brothers. She was happy, I think. She filled her time as she liked and had a home health aide in her later years to help with household chores and personal care needs. In her senior years, she was finally the one being cared for, no longer the caregiver.

In 2020, my father relocated from China to live with Nai Nai as the pandemic raged. He was an anchor for her through those years, even if they struggled at times, each with strong opinions often held tightly. My mother joined them in 2023 for 6 months of the year, adding not just additional support but an emotional buffer to the people dynamics in my grandmother’s tiny apartment.

And in 2024, my family along with my uncles’ gathered for our first ever family reunion on my father’s side to celebrate my grandmother’s 100th birthday.

It was my kids’ first time meeting their great-grandmother (or Zhu Nai Nai as they call her) in person. But she wasn’t new to them. For several years prior, we had been doing weekly Saturday morning Skype calls to say hello. My kids don’t speak Chinese (I failed on that front), and so it was more of a brief 15-min nodding of heads with some light, poor translation from me. But I’d like to think it ingrained a few values that mattered in my children: honoring seniors, staying connected, and building in routines with meaning, to name a few.

My grandmother glowed during that visit. She was celebrated, doted upon, and the center of attention. She felt loved. I think it was a highlight of her life, seeing the family she built around her.

In the past year, my grandmother’s health started to decline. Her cancer returned and spread. Her once clear memory became fuzzy. Her fears started to guide her behavior, raising her suspicions, eroding sleep, and increasing her demands of others. Many of the qualities that enabled her to survive trying times started to impede her ability to gracefully enter the final stages of life. Stubbornness and relentlessness didn’t allow her to accept that the end might be near.

I am grateful that once she started hospice care at home with pain relief, Nai Nai suffered less. I’m also in awe of my parents who have put aside years of their own comfort and retirement dreams to care for her. It may have been Chinese cultural duty, but it was their personal commitment and love that made them stay in spite of, at times, truly difficult conditions.

Nai Nai was still talking throughout the night, even in her last few nights. It’s as if her mind still had things to accomplish, tasks that needed attention. But as her body guided her to rest, I think she finally realized in her final hour with my father, she had accomplished so much and was leaving behind a tremendous legacy.

My Grandmother’s Lessons

When I think about my grandmother, I don’t simply feel love or reverence. I feel a deep connection to what I learned from my grandmother’s journey and her behaviors. They aren’t all DO’s. There are some DON’Ts, too — because we can learn just as much from what doesn’t work as what does.

1. Focus on what matters and keep moving forward

Self-pity isn’t productive; action is. My grandmother had to make many difficult decisions in her life. She prioritized survival, her family's well-being, and, finally, her own happiness, choosing what mattered most in each season of life. And once she made a decision, she didn’t look back. She focused on moving forward.

Leadership Lesson
Priorities shift over time. The leaders who succeed are the ones who recognize the change and adjust their focus. They don’t waste energy ruminating; instead, they preserve their ability to navigate what lies ahead.

What’s one priority you need to re-evaluate? Stop avoiding the task. Schedule time to make a decision and move forward.

2. You don’t have to be alone

Even when all of her kids were across the globe, her only one of her grandchildren could speak so-so Mandarin (me), and gradually all of her friends passed away, Nai Nai didn’t choose to be alone. She sought out and found a few remaining family members in China (a maternal uncle and a maternal cousin). She welcomed thoughtful neighbors and community groups who periodically checked in on her. They brought small treats and made small talk. She didn’t push them away. She chose to get the support she needed.

Leadership Lesson
Leadership can be lonely. The weight of responsibility, the difficult decisions, and the confidential nature of the work. But you don’t have to go it alone. Trusted colleagues are there to support, and you can always bring in outside help: a coach, a therapist, a mentor, or all three.

Do you feel alone? Make a commitment to connect with someone you trust. If you don’t have one, source one. But don’t wait. Make this a priority for next quarter.

3. Take care of yourself when you can

Nai Nai couldn’t prioritize all her health needs when she was in the throes of taking care of 8 people. She was in survival mode. But as she got older and the weight of caregiving disappeared after my Ye Ye passed, she put herself first. Your health should always come first, but as a working parent leader, I know that it’s easier said than done at times. So do what you can, when you can.

Leadership Lesson
It’s never too late to take care of yourself. And if you don’t, no one else can help you.

What is one thing you could do to improve your health (mental or physical)? Start there. A doctor’s appointment. A 15 min workout. A 5-min stretch session. Don’t make it hard. Make it small and doable.

4. Enjoy what you can, when you can

Nai Nai has always loved food. She was a great cook and had a bit of a sweet tooth. In those early years in Taiwan, she and Ye Ye had to forego so much. So later in life, she was quick to ask for sticky rice with red bean or a pastry. She chose to savor what gave her joy. I’m convinced it was one of the reasons she lived so long — she enjoyed living.

What do you love about your work? What can you do to inject more of it into your day? Delegation, rescoping, and hiring additional talent. Be creative and be committed to making room for what lights you up. Do the same for your top talent and you’ll create a workplace that no one wants to leave.

5. Know when to let go

Nai Nai did this well earlier in her life and less so later in life. When she left China, she didn’t know she’d never see her mother again and wouldn’t be able to reconnect with any family until 30+ years later. But she knew to let go so that she could build a new life. When she was in her final year, she struggled to let go. She was so scared of death and beyond that she wouldn’t sleep, which added to her discomfort and stress.

Leadership Lesson
You can’t move forward if you can’t move on. Give yourself and your team the ability to move forward — let it go.

What are you holding on to that you should let go? A business idea, a team member, a decision that didn’t work out. Create a ceremony, journal your reservations, or talk to your coach or therapist.

6. You’re stronger than you think

Nai Nai faced terrible hardships throughout her life. They were made more stark because she was surrounded by comfort in her early years. But she made it through all of it. She had tremendous self-confidence and a belief that she could overcome anything.

Leadership Lesson
There will come a time when you don’t feel you’re equipped to do what it takes. Perhaps you’re behind on goals, or you’ve made a series of decisions that didn’t pan out. It’s easy to draw negative conclusions and to get demotivated. Your team needs you to stay strong.

Do you have anything making you feel down? If you need a moment for a pity party — do it. But then get back to it. Remind yourself of all you’ve accomplished and how you’ve navigated challenges in the past. You can do it again.

7. Don’t avoid change, embrace it

When I realized I wouldn’t be able to visit Nai Nai with my kids for several years, I asked my parents to buy her a computer and teach her to use Skype. She was 86. She didn’t complain. She didn’t resist. She didn’t worry about what was going to happen. She just learned how to take a video call with her granddaughter and her great-grandchildren. She wasn’t tech-savvy, and she didn’t need to be. She focused on the purpose of the tech and opened her mind to the possibility it was worth trying.

Leadership Lesson
AI, robotics, virtual reality, and more — there will always be a new technology out there. If you stay focused on your customer and team needs and stop worrying about constant change, you’ll choose wisely, learn what you need to learn, and invest in what your organization needs.

What are you overthinking? Can you take a simpler approach? Break the problem down and move forward with it in small chunks. Don’t let your fear decide what you do. That’s how the worst decisions are made.

Your Turn

My Nai Nai wasn’t perfect. No leader is. But she modeled essential leadership qualities that I emulated as I grew and evolved as a leader. And she was a grounding force when I faced adversity.

“Nai Nai survived. Nai Nai made it happen. I can, too.”

Too often, we think of leaders as people with big titles who lead large organizations. But as I get older, I realize that we have model leaders all around us, in our personal lives and in our community as much as in our professional ones.

Who have you looked up to as a role model leader? What did they help you realize and learn? I’d love to hear more in the Comments.

And if this post resonated with you today, please consider giving it a ❤️ and sharing it with someone who matters to you to help more readers find it and benefit from my Nai Nai's wisdom. May she rest in peace.

Thank you for joining me this week.

May you lead without limits,

I’ve never met a team that didn’t have issues with conflict.

It could be a leader who talks over everyone in a conversation. Or a long-tenured, senior expert who inspires enough fear in everyone to manipulate every decision. Or it’s isolated to two people who interact like oil and water, and disrupt every meeting.

Perhaps this resonates? If you’re being honest, I’m guessing you can name a few issues on your team.

Conflict isn’t in itself bad. As a leader, you know that.

But you also know that some types of conflict on your team don’t feel like the kind that is like medicine and will lead to good outcomes.

Too often, leaders want to jump to the solution. But unless you know the root of the issue, you risk addressing the wrong problem.

My recommendation is to start with a diagnosis.

How a night out with friends can help you diagnose the source of your team’s conflict.

I find that an analogy can sometimes help you achieve a helpful emotional distance from a problem.

If you’re like most leaders struggling with conflict on your team, you will literally feel your blood pressure rise as you think about the different issues and how they are hurting your organization and your goals.

So bear with me as I take us through one such analogy that has helped me:

Most of us have grown up with a group of friends. High school, college, and those roaring twenties. For many, these groups aren’t just a source of emotional support; they’re a source of fun activities.

When I think back, one of the things I loved doing with my friends was going to a party — a dance party.

But the process of going to a party wasn’t always easy.

• We sometimes had trouble choosing a party

• Some friends didn’t want to go to the party we chose as a group

• When we got there, some might not know the dance moves

• Even if you know the moves, you aren’t dancing in sync

• And if you wanted to switch partners, good luck. It was often difficult and a risky move. You might end up not clicking with anyone else

The point of a night of dancing with friends is simply to let loose, enjoy the music, and each other’s company. Everything above is the opposite — tension-filled, angst-inducing, and fun-zapping.

And it all maps well to team conflict:

• Can’t choose a party —> Lack of shared vision and goals

• Don’t want to go to the same party —> Misalignment of personal and organizational goals

• Don’t know the moves —> Unskillful interpersonal engagement

• Are not in sync —> Lack of behavioral norms and expectations

• Switching partners is awkward — Individual differences get in the way

These are the 5 ways most teams sink their performance even before they get started. Even if it is only a subset of the group that is the cause, their negative interactions contaminate the entire group.

To help you diagnose what’s happening in your team, let’s go a little deeper into each one.

The 5 Sources of Team Conflict

I outline the five sources I’ve found most common through my leadership and coaching experience. In addition to signals, I share one path to help you move forward. Each person and situation is different, but these have proven to work over and over again.

1. Lack of Shared Vision & Goals

When the team doesn’t know where they’re headed and why, it’s hard to be in alignment day-to-day.

Signals

• Your team is struggling to know what to prioritize

• They fight over one area being more important than another

• When you ask one person to name company goals, they answer differently from another teammate

One Path Forward

Take the time to clarify where you’re headed and why. Use scenarios to help make them clear — for yourself and your team. Everything sounds great until you start to apply it to real-world scenarios.

Start with a document to organize your thoughts. Chances are, you already have your goals written down. Add scenarios and examples. Then, the key is to incorporate conversation into your process. When people have a chance to engage live, that’s when you’ll learn if the direction you’re setting will hold up.

2. Misalignment of Personal & Organizational Goals

Sometimes, your team knows what the organization’s goals are, but they don’t align with their individual goals. Maybe someone wants to work less, but the organization needs people who are willing to push harder. Or the person wants more growth, but the organization is in steady-state or even downsizing.

Signals

• They consistently push a particular approach, regardless of context, complexity or relative importance (e.g. faster, slower, bigger, etc)

• They seem disengaged in the work and/or irritable

• They are argumentative beyond productive dissent and criticism

One Path Forward

Document your observations. Check with others what they have observed without asking leading questions. If you see a pattern, approach HR and discuss a path forward.

More likely than not, it means having a conversation with the person 1:1. Don’t hide your concerns, and don’t assume why they are behaving the way they are. Be curious and ask. And offer them the opportunity to share that they may not be aligned with the organization.

Even someone who is senior, long-tenured, or historically well-aligned can shift. And that’s OK. What you need to do is help them communicate openly about the shift, if they have shifted, and to align on what to do next. And if something else is the root issue, having this conversation will help as well because it’ll get at the root of a set of behaviors that is disruptive to the team.

3. Unskillful Interpersonal Engagement

Sadly, most professionals don’t get training on how to collaborate productively. Even if someone is a seasoned, experienced leader, it does not mean they are skillful in interpersonal engagement. Perhaps they didn’t need to be in prior roles, or others compensated around them.

Signals

• They struggle to listen actively and instead, speak over others or take up all the air space

• They avoid difficult conversations, either deprioritizing them or delegating it to other people

• When they engage, others leave the conversation deeply frustrated not simply based on what they discussed, but moreso how they choose to approach the topic (e.g. heavy handed, unclear communication, accusatory tone, etc)

One Path Forward

Given the person direct, and clear feedback where you outline their observed behaviors and the negative impact. Consider getting them a leadership or communications coach or sending them to training that will directly address their specific challenges.

Whatever you do, don’t wait. The longer you let their behavior persist, the more you are indicating to them and those around them that their behavior is acceptable. That is a surefire way to lose top talent.

If you find that it isn’t just one person, but a group of individuals who are challenged (possibly in different ways), then group coaching, 1:1 coaching, and/or group training may be necessary. The reality is that each person needs to up level, but they also need to be aware of how they may be triggering each other. No one exists in a vacuum; don’t treat the issue as if it can be easily quarantined.

4. Lack of Behavioral Norms & Expectations

Sometimes, your people aren’t being unskillful; they keep bumping into each other because they don’t know how to get in sync. (Imagine a group of people doing a line dance, but in completely different directions — it’s a mess!)

Signals

• People are talking past each other because they are at different stages of a process (e.g. one person is brainstorming, while another trying to plan)

• There aren’t clear roles and responsibilities and so people stepping on each other’s toes

• Critiques are becoming personal, and cliques are forming; meetings are starting to feel like a middle school lunchroom

One Path Forward

Draft a Code of Conduct and outline the behaviors you expect from the team. Invite discussion and conversation around the draft, including soliciting edits and additions. You’re not operating a democracy, but getting input is a helpful way to make sure you aren’t missing anything or misstating an idea. It’s also a way to build buy-in from your team.

One concept to include is “disagreeing and committing.” This allows everyone to commit to decisions even if they expressed dissent, and it ensures cohesion when the team starts to execute. It’s helpful for day-to-day operations. It’s also essential to align on the Code of Conduct (because, let’s be honest, not everyone will agree to every point) and move forward.

5. Individual Differences Get in the Way

Even when you have common standards of behavior and the same “dance steps” shared across a team, each person will still have their own style: of thinking, of communicating, of processing, and of disagreeing.

Having differences across the team is usually a great thing. The only time you need to address it is if it starts to impede progress and create unproductive tension.

Signals

• Someone becomes immovable in demanding that collaboration proceed a certain way, and always in that way

• Two people have different communication styles and are not hearing each other when they speak, and struggle to find a way to reach the other person

• Team members are starting to gossip about another teammate and their different approach to a body of work, but they aren’t approaching that team member

One Path Forward

The key to this issue is to address it early and before it develops into a pattern or theme. You don’t want anyone to become a target of ridicule or avoided because their reputation precedes them. This is true of the most junior person on the team or the most senior.

Don’t wait to dive into this one. It might feel more risky because it requires delving into a particular person’s style, but that doesn’t make it less worth addressing. It makes it even more powerful. Because of your intervention, that person may have a far more productive career future because you helped them get the feedback they critically need.

Your Turn

If you’re like most leaders, unproductive interpersonal conflict is just one of many issues on you long list of to-do’s.

It truly might not be one of the most urgent and critical things to solve, but it’s probably also costing you and your team more than you realize — not just in lost productivity at work, but in sleepless nights or at least more irritated commutes and dinner times.

If you’re not sure where it stands, talk to your team. Or just pause to observe what’s happening in your team’s interactions. What might realize may surprise you. It might not be an issue that is simply caused by your team’s lack of skillfulness or style differences.

The source might even be you. This your invitation to assess the situation before a truly negative outcome emerges.

If this piece was helpful to you, I’d deeply appreciate your sharing it with another leader.

I write each week about the topics I knew made a differentce for my teams and the businesses I led, but felt challenged by as a leader. With my newfound 20-20 perspective, I want to help more leaders make better decisions and build stronger organizations.

When you’re a leader of leaders, it’s that much more important to invest in your people and how they interact. If you’ve found ways to diagnose (and address) the type of team conflict that derails, I’d love to hear it in the Comments. I read and respond to every one.

And if you have a minute to give the post a ❤️, you’ll help more people find it on Substack.

Thank you for joining me and 2,000 other leaders on the journey to lead without limits,

It’s time for your weekly virtual team meeting.
You’re 2 min late as usual, and rushing in from another conversation.

The agenda is set. It should be routine, and you’re hoping the team brings a bit more energy today.

They’ve been dragging. It’s been intense, but there is a lot more to get done. You need everyone to show up and show up strong.

As you open the meeting and dive into initiatives, everyone seems to be paying attention, but when you ask if there are questions or alternative ideas, no one adds anything. The few that speak up only add “everything looks good.”

You push back on one person’s ideas, and she hesitates as if wanting to respond, but then acquiesces. You don’t notice it, but a few people’s eyes dart down, and it looks like they are typing. You chalk it up to note-taking.

You think you’re having one meeting. But there are actually two in motion: the one you see and the one you don’t.

Right alongside your meeting.
Everyone in your team is in it, but you.

Why?

Because they don’t trust you.

What’s even worse?

You have no idea.

You’re not alone. Most leaders have no idea when they’ve eroded trust and removed the conditions for psychological safety.

And to be honest, some don’t care.
This post isn’t for them.

This post is for the leaders who do care.

The ones who want to create an environment where their team can be successful and enjoy the ride. The ones for whom it isn’t just about the results, it’s also about relationships.

The good news is that you can do something about it — if you know what to look for.

But let’s start with why psychological safety matters.

Lack of psychological safety will sink your team’s results.

The research is clear:

When people are scared, they are less able to process complex ideas, less creative, and less likely to be happy.

In short, they’re less likely to perform well and less likely to enjoy the work. All the things leaders try to avoid when creating a productive workplace.

In the example above, it means fewer ideas, less dissent and debate, and more side conversations and gossip, which further erodes trust and creates more cognitive and emotional load — load that no one can afford.

So what does psychological safety even mean?

Let’s start with what it isn’t.

It doesn’t come from constant praise. It doesn’t mean giving people a pass every time they make a mistake. It doesn’t result from avoiding critique and hard conversations.

As defined by Harvard professor Amy Edmondson, who coined the term:

“Psychological safety is a belief that one will not be punished or humiliated for speaking up with ideas, questions, concerns, or mistakes, and that the team is safe for interpersonal risk-taking.”

Even if your organization has high standards and is not tolerant of underperformance, you can create an environment that has a healthy level of psychological safety. Because at its core, psychological safety is about how you relate to each other — not technical skills or performance outcomes.

The leaders who create the conditions for psychological safety well understand this. They hold their teams accountable for performance while also creating ample room for interpersonal risk-taking.

But not every leader chooses to invest in psychological safety.

Why highly successful leaders don’t prioritize psychological safety.

There are many reasons why psychological safety doesn’t show up in leaders’ top priorities. I can’t cover them all, but I will highlight of what I’ve found to be the most common.

1. Creating psychological safety is not a prerequisite for success.

The old adage that you learn far more from failure than from success is an apt description of why so many leaders are blind to psychological safety.

Many leaders rise because they were in the right place at the right time. I’m not saying they didn’t earn the raise or the promotion. But sometimes they don’t encounter the diversity of situations and build the skills necessary to be an extraordinary, well-rounded leader.

When you are making great progress, even if it requires significant effort, you may not be aware of all of the elements that contributed to the foundation for your success.

It’s the gift and the curse of fast or smooth success, despite the research I cited above.

2. Overemphasis on outcomes over output.

Many organizations and leaders put too much focus on results only. It’s true that if you don’t achieve your goals, all the processes and activities you put in place may feel less relevant.

This can mean skipping over the behaviors and relational norms that help your team achieve those results in the first place and sustain them.

3. Some leaders were “raised” in work environments where psychological safety wasn’t part of the culture.

So they perpetuate what they know best.

Whether it be walking on eggshells with a facade of “politeness and niceness” or a rough and tumble, “survival of the fittest” model or something else altogether that stifles connection and smoothers direct conversation, some leaders just don’t know what they don’t know.

Regardless of the reason, once you realize the psychological safety is something that could help your team improve how it works, know that you can develop your ability to gauge whether your team is lacking in psychological safety.

Here’s how:

The signs are obvious only after you start to see them.

Like so many things in life, once you start to see them, you won’t be able to stop.

1. You receive little critical feedback

2. Your team doesn’t offer dissenting views

3. You are always right if there is a debate between you and your team

4. Your employee survey results are negative, but you don’t know why.

5. You don’t meet 1:1 with your direct reports (your EA or Chief of Staff is always present)

6. You don’t create time 1:1 or in group meetings to receive feedback.

7. Your team only shares examples of when things go well

8. You don’t know much about what matters to your team outside of work

9. Your team doesn’t know much about you and what matters to you outside of work

10. You get subtle suggestions from your team or colleagues to be more positive or to give your team time.

11. You feel like you’re carrying all the load for the team

There may be other signals as well, but this list should give you a good start. If you are experiencing 2-3 of these, it’s time to dig deeper.

How do you know it’s actually an issue?

You won’t know for sure until your team tells you.

But you likely have a sense that something is wrong. Your team is more quiet than outspoken. They say “yes” much more than they say “no.” You sense that the team’s work could be better, and they could be more engaged, more energized.

The only way to find out is to hear it from your team. Here are some ways to find out:

1. Talk with your team either as a group or 1:1 — Share your concerns and ask if they are seeing an issue. This requires finesse and judgement on when and how you broach the subject. But don’t overthink it and don’t delay.

2. Talk with trusted colleagues — Your team doesn’t work in a silo. Ask cross-functional partners what they are hearing and experiencing. Sometimes, you just need a different perspective.

3. Be patient. Slow down and make space — Don’t wait to start the conversation, but also don’t expect all the answers to come pouring out. It took time create fear, and it will take time to eradicate it. The surest way to kill this process is to add more pressure to it.

4. Be vulnerable — Share more about your thoughts that might feel counterintuitive or surprising. Do it concisely so that you don’t suck up more air space. Model what it means to put yourself out there. If your team sees it, they are more likely to mirror it.

5. Hire an outside coach or consultant —Sometimes you need a third-party perspective and voice. Your team may not be ready to open up to you, but they may be willing to reveal what is happening to someone outside your team. Just make sure you are clear about ground rules from the get-go: what will be kept confidential, what will be shared, and how you all will move forward.

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Creating psychological safety is a marathon, not a sprint.

Similar to long-term health strategies, it takes time to see results from attempts to build psychological safety. People need time to build trust and new habits.

You’re helping your team shift their assumptions: from speaking up will result in a bad outcome to seeing that it will result in better performance individually and as a team.

These are not small shifts. They require practice, observing outcomes, and internalizing both. It could take weeks, it could take months.

The key is to keep dialogue open, continue to reiterate why it matters, and to recognize and reward the change in behaviors you want. The only way people will believe the shift is real is if they experience the benefits and witness evidence that demonstrates that what you say is true. And this needs to happen consistently and regularly.

Your turn.

I’d love to hear more about what has worked for you to create psychological safety in your team. How did you know something wasn’t working? What did you to change the dynamics? What felt obvious and what didn’t?

When you share your experiences, you help everyone in the Lead without Limits community grow. And you help more leaders create the kind of organizations we all want to work in.

Thank you for joining me this week. If this post resonated, the kindest thing you can do is share it with someone who needs it and give it a ❤️ so that more leaders can find it on Substack.

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And in case you enjoyed my Substack Live with Tom Hardin, I’m so excited to announce that his book Wired on Wall Street is now available for purchase. I got my copy last week.

May you lead without limits,

On the face of it, it was a dream team.

Senior, proven leaders with decades of experience.

They were transforming a company, shifting it into growth mode and making it transaction-ready.

They showed up to meetings on time. They came to a decision quickly. They were aligned on the next steps, and people shifted into action seamlessly.

And yet when it came to their collaboration, something seemed off. They contemplated few ideas. Very little was debated, especially highly strategic decisions. When there was dissent, it was about minor topics like the formatting of a deck or the timing of a meeting.

They were going through the motions of execution well, but their results were mediocre, and they weren’t improving.

When the leader came to me to help him and his team achieve higher performance, he had no idea what was brewing under the surface.

After the first few sessions, it was clear to me — this was a team that deeply feared conflict, with their leader and with each other.

What felt like safety was costing much more than each person realized. Without conflict, they were missing out on better ideas, smarter solutions.

Even worse, they were creating a culture that drained everyone’s energy walking on eggshells. Left unaddressed, the team would fall apart.

The good news? It wasn’t too late to fix.

Conflict isn’t a sign of risk. Misunderstanding it is.

Conflict gets a bad rap. It’s associated with wars and physical violence. It’s something culturally we teach people to fear and avoid.

And yet conflict can support problem solving, creativity, and innovation. Technological advancements, scientific discoveries, and creative endeavors often require productive friction to source diverse ideas, debate merits, experiment and test, and overcome setbacks.

So why does conflict trip us up?

Because not all types of conflict1 are productive, and most teams don’t take the time to identify which one needs addressing:

• Task conflict (disagreements about what to do or how to think about a problem) can lead to better decisions, more creative solutions, and higher quality outcomes — when managed well.

• Process conflict (disagreements about how work gets done, roles, resource allocation) is correlated with a decline in team respect and trust, as well as reduced team productivity and viability.

• Relationship conflict (interpersonal friction, feelings of dislike or disrespect) is almost always detrimental. It erodes trust, increases stress, and hurts performance.

The teams that navigate conflict well are the ones that understand the difference between each category and know how and when to address each.

The ones that struggle can’t distinguish between them and allow a task or process conflict to transform into a relationship conflict.

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Where to start and why.

• Build awareness and a common language around these different types of conflict. With a shared understanding and common language, it’s much easier to get alignment on why this matters and make the changes necessary.

• Take the time to discuss openly how conflict is impacting your team. Invite the team to share examples of where the team isn’t able to focus or execute well together because conflict is distracting or stalling progress.

• Commit as a team to improving how you navigate conflict. This needs to be a group commitment because conflict can arise at any time and with any configuration of people. Any efforts to effect change will be lessened if only a subset of the team is ready to engage.

• Learn how to identify the different types of conflict. Use specific examples and discuss them. Only when you get into particular examples will everyone develop the muscles to identify them as they emerge.

• Discuss how to navigate each type of conflict more effectively. This will be specific to each team, but will generally center around roles, responsibilities, goals, constraints, and acceptable norms. One of the most important elements is clarifying who the decision-maker is and how that gets determined for each situation.

• Make it safe to call out when you’re starting to drift from one type of conflict to another and to pause before continuing. The pause gives everyone engaged a chance to step back, away from the fray, calm their emotions and get some perspective. Are you slipping into relationship conflict when the real issue is process? Is someone getting caught up in a process element when another person is focused on task? Just the act of pausing can help everyone get back on track.

This might feel like a lot to work through to just get started, but when you are dealing with group dynamics and trying to correct unhealthy norms, you need to be thoughtful about how you set the foundation.

As you set up your guidelines, don’t worry about creating hard and fast rules. Just start with a few scenarios and create guidelines organically. The key is to get started and open up the conversation. Simply acknowledging that there is an opportunity to improve can help the team create more productive habits.

Your turn.

Most teams in my experience spend 90% or more of their time focused on the “what” of their work. Few take the time to step back and align on what I call “meta topics” on “how” they do their work, like conflict management. These conversations require thoughtfulness and a pausing of the work that feels uncomfortable.

But it’s exactly these types of topics that, when left unaddressed, can become a terrible distraction at best and a highly destructive force at worst.

I’d love to hear if you have spent time on your team talking about the “how”. And if conflict management is one of the topics you’ve addressed.

If you haven’t, may this post be your invitation to start the conversation. I’d love to hear what emerges.

If you found this post helpful, I’d greatly appreciate your sharing it with others who you think would find it useful.

And if there are other topics you’d like me to cover around team dynamics, please reply and let me know. I read every message, even if I can’t respond to them all.

May you lead without limits,

To build it. Tear it down. Reconfigure it. Build it again.

That eight-year-old girl grew up to build the longest floating bridge in Iraq, command an 800-person battalion in Afghanistan, and earn a PhD in engineering. And somewhere in the middle of all of that, she also figured out how to defeat the most dangerous enemy she’d ever face.

Not the ones shooting at her base. Not the assassination attempts.

The mean little voice inside her own head.

That’s Jenn Donahue — engineer, Navy Commander, author — and last week she joined me for a Substack Live that I’m still thinking about.

Here’s the thing: I brought Jenn on because I knew her story was extraordinary. What I didn’t expect was how much it would land for the high-achieving leaders I write for every week. Because what she walked through, the success, the dark chapter, the clawing back out, this is the arc I hear over and over again in private conversations with senior executives. It’s not what you see on social media or in press features. But it’s what people are actually living. I know, I experienced it, too.

The details may look different. But the experience of being beaten down when you’re already carrying enormous responsibility, and then arriving home and finding nothing left of yourself? That’s not a military story. That’s a human story.

The Hardest Battle

In Afghanistan, Jenn was responsible for 800 people. Housing. Food. Safety. Everything. And at the same time, she reported to a leader who spent seven months systematically tearing her apart.

“He almost seemed like the enemy,” she told me, “and not the people who are shooting at us.”

She tried to make a game of it — putting tick marks on a whiteboard during meetings, counting down how many were left. She shielded other officers from the worst of it, becoming a kind of umbrella for younger leaders who needed guidance they weren’t getting from him. She protected everyone she could, even peers.

By the time she came home, she was completely emptied out. The glass-half-full person had nothing left. No joy. Nothing.

“I had to try to claw myself back out of that hole and try to find who I was before I left.”

She admitted she probably should have gotten help. She didn’t.

Instead — being an engineer — she started taking apart her own thoughts the way she would take apart a structural problem. And in doing so, she built something even stronger.

The 3 Voices in Your Head

Jenn started with identifying 3 different voices she heard regularly in her head:

MEAN LITTLE VOICE. This is the one who doubts you. It makes you question yourself: Can I really do this? Am I good enough? Someone else knows more, has more experience, is more likely to be successful. This is the one that keeps you small because it’s trying to keep you safe.

SNEAKY LITTLE BASTARD. This one distracts you. It finds ways to take you off your game by giving you reasons to delay, avoid, and stop staying focused on what actually matters.

THE WARRIOR. This is the voice that is clear, calm and knows the right thing to do. It’s the one that knows what you’re capable of, doesn’t think small, believes in you, and can do the work to achieve what you actually want. This is what Jenn was able to access more of through the framework she built.

The Warrior Framework: Four Steps that Changed Everything

Once she identified the voices, Jenn went back to what she knew: military rules of engagement. The same protocol she learned to identify and respond to a physical enemy. She wondered: “What if I applied this to the voices in my head?”

Here’s what emerged. She calls it Perceive, Assess, Ready, Act.

PERCEIVE. This is situational awareness — but for your inner world. What voices are actually running? Instinct? Intuition? The mean little voice? The warrior? Most of us have never stopped to notice there are multiple conversations happening inside us at once. Step one is just paying attention.

ASSESS. Friend or foe? In the military, you assess what’s coming at you before you react. Same with your inner voices. Is this voice rational? Is it genuinely protecting you — or is it just trying to keep you from feeling discomfort by keeping you stuck? Assess before you respond.

READY. This is where Jenn says most people get tripped up. You can acknowledge the mean little voice all day. But if you just stomp it down without engaging the warrior, it comes back louder. The Ready phase is about activating your internal warrior — your track record, your evidence, your accolades — so she actually has something to fight back with. “Warrior, wake up. You’re on the bench. Get off. We’re going into battle.”

ACT. One small, calculated step. Not a leap of faith. A step. In the direction of the goal, the dream, the thing you’ve been hesitating on. “A plan is great until the first shot is fired” — so don’t let the plan become an excuse not to move. Just move.

Why This Model is Different

I’ve seen a lot of inner critic frameworks. Most of them tell you to acknowledge the voice, then move on. And Jenn is clear about why that doesn’t work: if you just stomp it down, it comes back. Louder. More frequently. Harder to quiet.

The difference in her approach is that you have to understand why the voice is there in the first place. And then you have to counter it with evidence. Real, specific, written-down evidence.

This isn’t soft work. It’s backed by neuroscience. Jenn spent months reading peer-reviewed research — going three sources deep, as she was trained to do — before she built her framework.

The finding that stuck with me: when you physically write something down by hand, you engage multiple parts of your brain in a way that typing or thinking just doesn’t. Your brain actually begins to rewire.

The Practices that Actually Work

These are the specific tools Jenn shared that she used herself and now uses with clients:

• Write down one win per day. By hand. Doesn’t matter how small. Woke up on time. Closed a deal. Cooked a good dinner. After about a month, your brain starts to look for the wins instead of cataloging the losses.

• Write down your full list of accolades. All of them. Going back as far as you can remember. This is your evidence. When the mean little voice says you can’t — this list says otherwise. Read it. Internalize it. That’s your warrior right there.

• Find a Battle Buddy. Someone who knows your track record. Someone the voices can’t reach — because the voices live only inside your head. Your battle buddy sees what you can’t see in yourself yet.

• Stop focusing on failure. Start thinking about risk. Risk is a continuum — the probability of failure combined with the consequences if you do. Most of the time, when you actually do the math, the probability is lower and the consequences are smaller than the mean little voice has convinced you they are.

And when it comes to taking action: small, calculated steps. Celebrate each one. “This is my favorite part,” Jenn said.

Don’t make the plan so rigid that a missed step feels like failure. Make it flexible enough to keep moving.

On Being Fully Emptied Out

What stayed with me most from this conversation was Jenn’s willingness to describe what that dark period really felt like. She’s sunny. Bubbly. A glass-half-full person by nature. And she told us there was literally nothing left. No joy. Nothing. (If you watch the recording, you can feel it and see it in her eyes, in her tears.)

I think about the leaders I coach — and the leaders reading this right now — who might be sitting in something that looks a lot like that. Maybe not from a war zone. Maybe from a relentless boss. A job that’s slowly been hollowing you out. A season where you’ve given everything to protect everyone around you and arrived home with nothing left for yourself.

Here’s what I want you to hear from Jenn’s story: she clawed back. She didn’t just survive the experience — she turned it into a framework that now helps other people find their way back to themselves. The warrior was there the whole time. She just had to learn how to find her.

Yours is there too.

Your Turn

Jenn’s advice is rich with actions you can get started on today. Whether in you’re a dark place or feeling buoyant, there’s value in any one of the practices above. Pick one or start off by simply identifying your voices. Can you tell the difference between each?

I’d love to hear what worked for you or if you have questions about any of these in the Comments below.

Leave a comment

Stay Connected to Jenn

Jenn’s book “The Warrior Framework” comes out March 24th. Pre-order now at thewarriorframework.com and you’ll get early access to the first chapters, a free workbook, and a few other surprises. If you’re a leader who’s been fighting battles on multiple fronts and running low... this is the book I’d put in your hands.

You can also find Jenn on LinkedIn at Jenn Donahue, PhD, PE or at jendonahue.com. Ping her if you’re looking for an experienced leader to deliver a memorable and actionable keynote or workshop.

A Final Thought

I really enjoyed this conversation with Jenn. Her work mirrors much of what I’ve learned in my mindfulness practices and through the Positive Intelligence program. The idea of accessing your inner warrior or wise version of yourself was life-changing for me. If you’ve been worried that this was just woo-woo mumbo jumbo — I hope Jenn’s extensive scientific research makes you reconsider.

We all have these voices. The leaders who break through and reach their full potential and help their teams do the same are the ones who know how to access their warrior and how to quiet the rest.

Your warrior is always ready to guide you. It’s up to you to listen.

May you lead without limits,

TIMESTAMP GUIDE — Skip to What You Need

Use these to jump to the parts that matter most to you:

• 00:00 — Introduction to Jenn Donahue: engineer, Navy Commander, PhD, author

• 04:00 — How an 8-year-old’s obsession with building became a lifelong mission

• 06:30 — From Barbie Dream Houses to the longest floating bridge in Iraq

• 07:20 — The hardest part of Afghanistan: 800 people, enemy fire, and a tyrant boss

• 11:50 — What “fully emptied out” actually feels like after 7 months of being beaten down

• 14:40 — How Jenn started clawing back: applying military rules of engagement to her own mind

• 17:15 — Defining the enemies: the mean little voice, the sneaky little bastard, and the internal warrior

• 19:45 — How to amplify your warrior voice: writing wins, accolades, and rewiring your brain

• 23:10 — The battle buddy: why you need someone the voices can’t reach

• 24:50 — The Warrior Framework: Perceive, Assess, Ready, Act

• 30:35 — The neuroscience: why writing by hand actually rewires your brain

• 33:15 — Why “acknowledge and move on” frameworks don’t work — and what does

• 36:35 — Writing the book: how Jenn used the Warrior Framework to push through her own resistance

• 39:10 — Why you need a plan — and why it needs to be flexible

• 40:55 — Failure vs. setback vs. risk: Jenn’s reframe that changes everything

• 43:05 — If you’re stuck right now: the very first steps to take

• 44:45 — How to get the book, pre-order bonuses, and how to reach Jenn

Periodically, I have the privilege of hosting inspiring leaders in a live conversation. Watch the full conversation above. Read my synopsis below or scroll down to the bottom of the post to access a timestamped summary.

When Rob DeGisi introduces himself to his Wharton students, he doesn’t lead with his impressive resume. He leads with this: “I’m a husband, I’m a father, I’m a Boston College alum, a Wharton MBA, and a New Jersey guy through and through. But as long as I can remember, I live for the New York Yankees.”

That opening says everything about what matters most—and it’s a lesson that took him decades of career pivots, unexpected setbacks, and hard-won clarity to truly understand.

I had the privilege of sitting down with Rob for a Substack Live conversation that revealed the messy, human journey behind a career that looks polished on LinkedIn. What emerged wasn’t just a story about breaking into the notoriously opaque sports industry. It was a masterclass in resilience, adaptability, and redefining success on your own terms.

The Accidental Path into Sports

Rob’s journey started as an accounting major at Boston College—not because he loved accounting, but because his father and older brother were accountants. He had no idea what he wanted to do. But he was part of the student radio station, broadcasting BC basketball, football, and hockey games.

The turning point came junior year when he was sent to Pittsburgh to cover a Boston College football game. As a 20-year-old coordinating booth setups, phone lines, press passes, and locker room access, he had a realization: “These grownups have pretty cool jobs.”

That observation sparked something.

Rob started networking before it was even called networking—making phone calls, sending paper letters, figuring out how to find a typewriter to type envelopes. He sent his third paper letter to IMG with a killer phrase: “I have aspirations for a career in the sports industry. However, I can contribute to your accounting needs right now.”

That letter worked. He got the call. And his advice for anyone trying to break into any competitive field? Focus your communication on what you can do for them, not why you find the industry interesting.

Every firm needs specific skills. Rob had accounting credentials, he’d passed the CPA exam, he’d worked at a big public accounting firm, and he was willing to move to Cleveland at 22 without knowing a soul. That combination got him his first job at IMG, where he spent four years in their television and golf divisions—all from a financial perspective.

But Rob realized something important: he was perceived as a finance person who happened to work in sports, when he wanted to be a sports business person who happened to have finance skills.

To make that pivot, he went to Wharton.

The Two Houses, No Job Moment

After Wharton, Rob’s plan didn’t quite work out as expected. He spent 20 months building relationships, heading to New York every other weekend for informational interviews. But by May 1993, he needed a paycheck—he had loans to repay. He took a job at CUC International, not in sports, but it’s where he learned strategic planning and direct response marketing.

Two years later, all that relationship building paid off. He got a call about an opportunity at the NBA. The guy interviewing him leaned back in his chair and said, “I’m not going to interview you. I already know you. You’re perfect for this job.”

Rob spent four years at the NBA, then moved to Bank One’s credit card division in Delaware, then eventually found himself at a startup salty snacks business in New Jersey. That’s where everything fell apart.

In August 2008, Rob moved his family from Delaware to New Jersey for what he thought would be a stable opportunity to grow. He bought a house in New Jersey but hadn’t sold his Delaware house yet. Within weeks, the CEO was kicked out by investors—the startup was burning through cash unsustainably. Then in September, Lehman Brothers collapsed and the global financial crisis hit.

“I owned two houses and had no job,” Rob said. “The fall of 2008 was awful. My last day wasn’t officially until the end of February in 2009. But it was a really difficult time.”

Fortunately, he sold the Delaware house in November. And he kept his salary through February. But the uncertainty was real, and it was scary.

What got him through?

The relationships he’d built over years. He joined a networking group of Wall Street professionals who’d lost their jobs. One of them connected him to someone who connected him to Copart, a public company in the automotive industry. By May 2009, he had an 18-month consulting gig leading their sports marketing initiatives.

The lesson: Relationships aren’t transactional. They’re insurance policies you don’t know you’re building.

When you invest in people without expectation, you create a safety net that catches you when everything else falls apart.

Redefining Success at Midlife

When Rob got laid off in February 2002 from Bank One’s credit card division, he went out on his own as an independent partnership marketing executive, working with clients like Citizens Bank and with the horse racing industry.

About a year into consulting, something unexpected happened. The marketing students at Wharton petitioned for a sports and entertainment marketing course.

The marketing chair asked Rob’s former professor (who Rob had stayed in touch with and guest lectured for) “Do you know anyone who could teach this course?” The professor recommended Rob.

Rob started teaching part-time at Wharton from 2003-2005 while running his consultancy. He taught what was then called a “mini” — a half-semester course. But it was hard to juggle both. After three years, he stopped teaching to focus on his busy consulting schedule.

Years later, he came back to teaching. And this time, it stuck. He’s now taught at Wharton for 11 years and has no plans to stop.

Here’s what struck me most: Rob doesn’t teach for the money. He teaches because it fills something in him that consulting alone couldn’t. “I might not have the second home like some of my classmates from Wharton do,” he said, “but I have this. And this is incredibly important to me. And you can’t buy this.”

The deeper truth?

At a certain point in your career, success stops being about accumulation and starts being about contribution. Rob found fulfillment not in what he could extract from his expertise, but in what he could give through it.

The Unsexy Middle of Any Journey

One of the most honest moments in our conversation was when Rob talked about the grind. Not the glamorous parts of working in sports, but the years of doing work that felt incremental, uncertain, and far from the highlight reel.

“There’s always doubt,” he admitted. “You wonder if you’re on the right path. You wonder if it’s all going to work out. But you keep showing up. You keep building relationships. You keep saying yes to opportunities even when you’re not sure where they’ll lead.”

This is the part of career journeys we don’t talk about enough. The unsexy middle. The years between early ambition and late-stage clarity where you’re just trying to figure it out.

The people who make it through aren’t the ones with perfect plans.

They’re the ones who stay curious, stay connected, and stay open to possibilities they couldn’t have imagined at the start.

What Rob’s Story Teaches Us

As I reflected on our conversation, three themes kept surfacing:

1. Relationships are the real ROI

Rob’s entire career has been built on relationships, not as networking transactions, but as genuine human connections. He doesn’t connect with people to get something from them. He connects because he’s genuinely curious about their stories. That authenticity is magnetic. And over time, those relationships compound in ways you can’t predict or control.

Harvard’s longest-running study on happiness confirms what Rob discovered through experience: relationships are the greatest predictor of health, wealth, and fulfillment. Not status. Not salary. Not even passion. Relationships.

2. Adaptability beats planning

Rob didn’t set out to be a Wharton professor. He didn’t plan to lose his job right after buying two houses. He didn’t know in 1983 that asking “How’d you get your job?” would lead to a 30-year career in sports.

He adapted. He stayed open. He followed curiosity over certainty. And that flexibility allowed him to build a life far more fulfilling than anything he could have designed at 22.

3. Fulfillment comes from giving, not getting

Rob’s consultancy is successful. But teaching? That’s where his passion lives. It’s where he feels most alive. Not because of what it gives him in status or income, but because of what he can give to his students.

As senior leaders, we often spend the first half of our careers accumulating titles, compensation, achievements. And the second half? That’s about contribution. About using what you’ve learned to make others’ journeys easier. That’s where real fulfillment lives.

What Rob Didn’t Share in Our Live Conversation

After the Substack Live, Rob and I debriefed and I realized we missed perhaps the most important piece of guidance that Rob gives his students — what made the biggest difference in his career: his life partner, his wife.

Without her, he wouldn’t have been able to navigate the pivots and challenges in his career. Her patience, her career, and her relentless support gave Rob and their family the support they needed as Rob discovered his path.

Choosing the right partner in life is as Rob puts it, the most important decision you’ll ever make. Having the right person by your side can lighten hardships, help you grow and develop, and help you savor the journey that much more.

Your Takeaways

If you’re navigating your own career journey—whether you’re just starting out, in the messy middle, or looking for what’s next—here’s what Rob’s story offers:

• Start with curiosity, not asks. Want to break into a new field? Ask people how they got there. Learn first, build relationships, and opportunities will follow.

• Invest in relationships without expectation. You’re not networking for transactions. You’re building a web of people who know you, trust you, and think of you when opportunities arise.

• The unsexy middle is where the work happens. Stop waiting for clarity. Stay curious. Say yes to opportunities even when you’re not sure where they lead. It won’t be easy, but you can do it. Keep showing up.

• Define success on your own terms. Rob could have kept chasing bigger roles and bigger paychecks. Instead, he chose teaching. He chose contribution. He chose fulfillment. What does success actually mean to you?

• Adaptability is a superpower. You don’t need a perfect plan. You need curiosity, resilience, and the willingness to pivot when life throws you curveballs.

Rob’s story reminded me why I do this work. Because behind every polished LinkedIn profile is a messy, human journey full of doubt, pivots, and hard-won wisdom. And when leaders like Rob share those stories honestly, it gives the rest of us permission to navigate our own journeys with more grace and less perfection.

Your Turn

So here are my questions for you:

• What would it look like to redefine success not by what you accumulate, but by what you contribute?

• What would change if you treated your career not as a ladder to climb, but as a course to find—one that’s uniquely yours?

Take a moment to reflect and reply or share your thoughts in the Comments. I read every response.

Connect with Rob

You can find Rob on LinkedIn and on his website: www.ironhorsemarketing.com. Follow him for meaningful insights on the changing sports business landscape. In addition to teaching at Wharton, he is also a strategic business advisor and a gifted keynote speaker.

If this conversation resonated with you, please consider adding a ❤️ so that more leaders can discover this post on Substack.

And if you know of a leader who could benefit from this post, please consider sharing it.

Share

If you’re a leader in the accumulation phase, the messy middle, or a later stage of your career, I welcome hearing from you. There is no perfect moment — just the one you’re in.

May you lead without limits,

Conversation Topics with Timestamps

Want to dive deeper into specific parts of our conversation? Here are the major topics we covered:

• [00:05:01] Early Career: From Accounting Major to IMG – How Rob discovered sports broadcasting in college and landed his first job at IMG through persistence and positioning his accounting skills

• [00:14:30] Breaking Into Sports: The Power of Asking Questions – Rob’s philosophy on networking: ask for information, not jobs, and build relationships authentically

• [00:21:45] The Two Houses, No Job Moment – The scary period when Rob lost his job after buying two homes and how his network became his safety net

• [00:28:20] Career Pivots: Teaching at Wharton – How Rob started guest lecturing and eventually taught his own course at Wharton while running his consultancy

• [00:35:12] Becoming a Wharton Professor – The unexpected journey from guest lecturer to teaching his own course on the business of sports

• [00:42:15] Teaching Philosophy: What Students Really Need to Learn – Why Rob closes every semester with “What I Wish They Told Me in 1987” and the life lessons he shares beyond the curriculum

• [00:48:30] The Unsexy Middle of Career Journeys – Rob’s honest take on navigating doubt, uncertainty, and the years between ambition and clarity

• [00:53:00] Redefining Success: Relationships Over Assets – Why Rob values his teaching relationships more than material wealth and what fulfillment really looks like at this stage of his career

Every week, a leader asks me, “How do I network my way into a new job?”

Sadly, it’s usually only shared with me when someone needs a job… badly.

Unfortunately, that’s one of the hardest times to build a relationship. You can do it, but it’s like trying to lower your cholesterol when you’ve had a heart attack.

You can do it, but it’s harder to make significant progress when you are climbing uphill with one arm tied behind your back.

You feel less confident about your path forward. You might have anxiety about the job search itself. Depending upon how long you have been searching, you might feel deflated and demotivated.

As I wrote last week, these sentiments don’t just exist within you, they seep out and can do the opposite of what you want: dissuading people from engaging with you instead of drawing them closer.

Needing a job and having a heart attack aren’t the same thing, but investing in your network is the same as investing in your health.

You want to be doing it early, often, and with the intention of making it sustainable.

And the good news is that it’s never too late to invest.

Let’s start with why you need to shift from viewing your network as a career tool to seeing it as a health indicator.

Humans have always been relational beings.

We live in communities, family units, and partnerships. It’s no wonder that we are wired to benefit from healthy relationships.

The 85+ year Harvard longitudinal study on adult development has found that strong, supportive relationships are the key to lifelong happiness, physical health, and longevity.

And yet, with the start of the Industrial Revolution all the way through the 2020 pandemic, our societal norms have made us more disconnected and isolated.

In June 2025, the World Health Organization (WHO) Commission on Social Connection released a report revealing that 1 in 6 people worldwide is affected by loneliness. This doesn’t just mean people aren’t happy; the research indicates that loneliness leads to major health issues and even death.

With this context, isn’t it time to start viewing your network less as a series of transactional relationships and more as the foundation of your relationship health?

Well, if I haven’t sold you on the health factors, let me give you a few more reasons why your relationship (network) strength matters to your career:

Only 4% of senior positions are filled through direct applications. 70-85% of executive level roles are filled through networking and headhunters. That means without a network, you’re going to have a much harder time landing your next role.

And if you want to have the option of making a pivot mid- or late-career, you likely won’t be able to do it without a network. Recruiters focus on what you have done, less on what you could do. Most professionals get placed in a deeper and deeper box over time. Your relationships are what will help you get out of that box.

Just as you might focus on mental health or nutritional health, relationship health is a predictor of your overall well-being in life and your ability to secure a fulfilling career.

Isn’t it time you start investing in it with the same level of intentionality?

The 5 different networking muscles to strengthen (over time).

Each of these deserves much more than a few lines, but this is nice digest of the areas you’ll want to invest in over time.

Choosing who.

This is likely the thing that stops most people in their tracks. If you’re advanced, there are quite a few ways to make this strategic, but for most people, my advice is start with who you know and who knows you. In the beginning, you want to feel comfortable first and foremost.

Reaching out.

Next up in the discomfort scale is sending the message and actually asking for someone’s time. It’s not hard unless you’re like the average person and can hear 5 different voices in your head telling you “why bother?” “they won’t respond” “you’re not worth their time” “they’re too busy.” How do you get past it? Nike had it right — just do it.

And what you’ll quickly learn is that the hardest step isn’t the initial outreach, it’s the follow up. Because most people are busy and will miss your initial message. So you’ll need to do it again, and again before you actually get something scheduled.

Having a conversation.

There are whole books written about this. David Brooks’ “How to Know a Person” is a good recent one. But I like to follow what my son learned in kindergarten: Listen. Make eye contact. Stay still. Share when it’s your turn.

Following up + Nuturing.

The art of the thank you note seems to have been lost somewhere in the last 25 years. It was standard when I graduated college in 2001, but I’ve noticed that after an interview, sometimes I don’t even receive an email. I don’t care what anyone says, it’s bad form. Show that you care and that the person you met mattered to you. Even if you won’t be lifelong friends or perhaps talk again, do them the honor of at least acknowledging their time. It’s the right thing to do.

How do you make networking routine?

One you know what you want to work on and strengthen, now it’s time to build the habit so that you can improve it over time.

Get clear on your why.
If overall health feels too abstract, and you want to stick with career opportunities as your raison d’etre that’s fine.

Just get clear on why you will invest the time in this part of your life. Without a clear reason, when setbacks arise, you’ll not only deprioritize this effort, you won’t be able to find a way to reprioritize it.

Create a schedule.
Just as you create a schedule for your other health activities, do the same for networking. It can be monthly, quarterly, or even every 6 months, but book time on your calendar.
What gets scheduled gets done.

Make the steps smaller.
When you break down the big actions into smaller ones, you make it so much easier to tackle. If you feel any resistance at all, don’t aim for outcomes. Aim for outputs. In a world of OKRs that prioritize outcomes, it’s easy to get overwhelmed with big goals.
By focusing on small outputs, you build momentum with less drag.

Set milestones.
When you have goals, it’s much easier to stay focused and on track. It isn’t enough to simply say you are going to network more. Some milestones that have worked for me include: # of outreaches, # of events I’m attending, # of groups I am joining and contributing to.

Quality matters more than quantity, but make no mistake, quantity matters, too. The key is to set a target that feels achievable, but will require some effort. And don’t worry if you don’t get it right the first time. You can always change these as you learn more about what works for you.

Celebrate any progress.
When we are building a new habit, we need more positive reinforcement to build our confidence and give us the energy to keep on going. One way to do this is to track your actions and reflect on them regularly. Start with weekly or monthly, and you might be surprised at how satisfying it feels.

Get an accountability buddy.
People who have a partner are 65% more likely to complete their commitment — that jumps to 95% when you have specific, scheduled check-in’s! The key is to find someone who is as committed as you are.
We go further together.

Overcoming the inevitable setbacks.

Even if you schedule time, set milestones, make your steps small, and celebrate your progress, you will inevitably face setbacks.
This isn’t a prediction, it’s a promise.

Whenever we start something for the first time, even if it begins with roses and rainbows, thorns and storms will eventually emerge:

• A harrowing time at work or at home will consume your time and attention and make you forget this entire effort.

• You’ll have a dry spell where it’ll feel like everyone is ghosting you.

• One conversation will go sideways, and you’ll want to crawl under a rock and never come back out.

• You’ll lose your rhythm for a day that then becomes a week that then becomes a month.

• Someone you know will land the perfect job, and you’ll wonder, “How did they do that? Is this even worth it?”

You don’t have to have a plan for all of these, but pick one or two and come up with a strategy for how you will respond before you face the setback. It’ll make it so much easier to get back on track if you do.

Here are some options:

• Focus on how you’ll help your network. Not the other way around. When it’s about them, it’s much easier to keep going.

• Don’t bite off more than you can chew. If it feels too hard, make the task smaller. Reduce the volume and slow the pace, but don’t turn off the faucet.

• Remind yourself that the stumbles are part of how you learn. No one learns how to walk without falling. You won’t learn how to make networking a habit until you make some mistakes.

• Get help. If you’re still not making progress, ask for support. If your accountability buddy isn’t able to give you the support you need, it’s time to call in some pro’s. Coaches abound in this area, as does free content on Youtube, Substack, and more. Don’t keep wandering, get directions.

3 networking activities to start in 2026.

So with all of this guidance, what are my top recommendations for 2026 to leaders who want to kickstart their networking:

1. Take stock of your network

Answer the following questions (Yes/No):

• I have 2-3 people I confide in regularly and can get unfiltered, helpful career support.

• I have connected with my current and former colleagues, clients and business partners on LinkedIn.

• I talk to someone in my network at least once a month.

If you answered Yes to all three, you’re in great shape.
If you answered No to any of the above, you have an opportunity to strengthen your network. Pick one and let that be a focus for the next 3-6 months.

2. Join at least 1 new group

If you don’t participate in an alumni group, mastermind, industry affiliation, or some other gathering that is connected to your career and the skills that matter to you, this is your sign it’s time to sign up.

And if more work-related conversations isn’t your cup of tea, then choose something that is more of hobby. The point isn’t just to connect with people directly in your industry. The point is to be connecting with people.

Like any muscle, your ability to meet new people and build relationships depends on you exercising the muscle. This is a great way to do it.

3. Attend one in-person gathering every quarter

Virtual gatherings are wonderful and help you stay connected when transit and travel are more difficult to access, but there is nothing like an in person gathering.

Simple things like how to stand, how to make eye contact, and when to shake hands sound easy, but when you’re engaging with new people and you are out of practice, it might be exactly the thing that trips you up.

Charlie Houpert, a charisma coach, talks about how you can enter a room as prey or as predator. The difference isn’t in just how you appear, it’s in how you feel and how you connect with others — either small and anxious or relaxed and engaged. You won’t become a predator by staying in your room.

So pick one in person gathering every quarter. You can find these through the community group you join, through friends, or through websites like MeetUp or facebook. Even your local library is an option. Don’t be picky, just show up and practice engaging.

Closing thoughts

All of this is great, but what if you’re in a particularly busy season of life — young children, elder caregiving, managing health challenges, or just in a state of transition?

It’s OK to deprioritize networking for a period of time. But like any health activity you sideline, if you wait too long to restart, your muscles will have atrophied and it will feel hard to get back going.

And if you do have the time, then don’t wait. Many of the relationships that have born the greatest opportunities for me (e.g. jobs, clients, an ego-boost, and meaningful friendships) were built over years.

Relationships don’t work like an on demand app. They are more like a fine wine, taking time to coalesce into something beautiful. Rushing the process doesn’t give you better results and sometimes, impatience can ruin the outcome.

Instead, trust the process: Build and nurture. Give and be patient. Over time, I promise you the results will be well worth the wait. The key is to get started and stay the course.

If you found this post valuable, consider leaving a comment or adding a ❤️ so that more people can find it on Substack. If you’re new, subscribe to never miss one of my posts.

And if you’re stuck trying to find a path forward, I have opened up 2 slots for Q2 coaching. Book a strategy session with me here.

Here’s to a another week worth savoring!

May you lead without limits,

The smell of desperation is repulsive.

I know. It isn’t a kind thing to say. But it’s the truth.

And when you are feeling scared in a job search, desperation is what creeps in. It’s what your inner saboteurs whisper to you:

• The clock is ticking

• Others are landing roles

• You’re just not that desirable

• No one wants you anymore

• You’ve peaked and the rest is downhill

You may feel like it’s all in your head, but it isn’t.

It seeps out into your interactions. It makes you furrow your brows, tighten your shoulders, forget to take a breath.

You start to be less present, let your anxiety drive your thoughts, and you don’t project confidence.

It’s scary. I know because I’ve felt it.

And I coach clients that feel it, too. Successful, type-A winners who are in the thick of it.

So what can they do?

Shift your narrative away from what you need to what they need.

The change feels small, but it’s actually enormous.

When you shift to what others need, you’re not just refocusing your attention. You’re implying something significant:

That you are complete and whole.

Sounds a bit woo, right?

It’s actually based on science: evolutionary, psychological, and behavioral.

• Evolutionary: We seek out people who will help us survive.

• Psychological: We want to be around people who will energize us, not drain us.

• Behavioral: We avoid people who may limit our autonomy because their fear and needs may dominate the relationship.

These are relationship-driven judgments, but they apply to the workplace just as much as they apply to other social environments.

We want to be around people who can help us be successful, not take advantage of us or limit us.

Start with figuring out who needs you and why.

Think about who you like to help and how you can support them. For example, if you’re a C-Suite leader, there are a variety of ways to frame who needs you and their needs:

• Customer needs:

  • Industry dynamics and competitive landscape

  • Consumer vs. B2B vs. other sectors (e.g. philanthropic, education, government)

  • New advancements and areas that are underserved

• Company needs:

  • Are they early-stage and needing someone to set up all the foundational elements?

  • Or have they proven the initial model and need you to scale it?

  • Or is it a turnaround situation where they need you to identify the issues and problem-solve?

When you have a clear understanding of who needs you and why, it’s much easier to frame why you.

Hone your narrative on what you have to offer.

When we think about what we have to offer in terms of who we are helping and why, it feels less like a sales pitch and more like a conversation of finding a match.

There are customers and organizations who need your skillset to help them address meaningful issues and create real value.

Your narrative should help them understand how you can do that.

Here’s a simple template:

You will ultimately say more when you’re talking with people or even sending a message, but this is a simple way to shift your narrative from focused on you (“I want…” or “I’m looking for…”) to focused on who you can help.

Then meet as many people as you can.

Once you have your narrative down, it’s time to test it out.
You won’t know how it lands until you try it on for size.

You’re not just seeing how others respond. You’re seeing how you feel saying it… out loud.

It’s amazing how much emerges when you say something out loud.

What you thought was the perfect framing can all of a sudden feel pushy, inauthentic, too buzzwordy, or just not quite right.

Don’t be afraid to tweak as you go.

The key is to keep going.

Every person you meet is someone who might be the connection.

Yes, you can be targeted about your approach, but to start, go broad and go wide. Chances are, you don’t know the person who needs you or who will know someone who does.

The power of human connections is real, but it’s also mysterious. Before you meet with someone, they won’t know what’s in your head, and you won’t know who’s in their life.

It isn’t only former colleagues or current business partners who might be relevant. It could be a friend with a shared hobby, a gym buddy, a family member, or even a neighbor.

This is why volume matters.

Forming a meaningful connection starts with curiosity, not a pitch.

So you schedule the conversation — woo hoo!

How you enter the conversation is as important as how you reframed your mindset from needing a job to wanting to help.

Relationships that last are built through mutual interest.
That starts with curiosity.

Sure you can share your narrative, but I recommend you spend as little time on you as possible. If they ask you, don’t be evasive — share away. But after you do a brief, emphasis on brief (like 2-3 min) intro, focus on them.

Get to know them and what matters to them. Learn about their career trajectory and what they aim for.

Even if you don’t find common ground, at worst, they may offer valuable insights and inspiration. At best, you’ll discover threads that allow you to go deeper and perhaps find a path to a person or organization that could be on the path to the people who need you.

Be relentless. Be thoughtful. Be patient.

This shift could take you a few minutes to make.
More likely, it’ll require practice and revisiting over time. That’s normal when you’re building a new habit.

The question isn’t how fast this will work. The question is how much more sustainable and energized you’ll feel during your search process.

The reality: it is taking senior leaders 12-18 months to land a new role.

By making this shift, you may shorten the time frame. But even if you don’t, you’ll be on a path to creating stronger relationships and a healthier mindset, both of which will help you in your next role and far beyond.

Thank you for joining me this week. If this resonated for you, please take a moment to add a ❤️ so that more people can find it on Substack.

Please also feel free to share it with someone who needs it.

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And if you want more from me, follow me on LinkedIn. I share advice every week like this one below:

Most execs wait too long to leave a failing company.

Wishing you a great start to your February!

May you lead without limits,

We started this Substack Live with technical difficulties, a fitting metaphor for our theme: disruption to reinvention.

Sometimes things break. Sometimes they break badly. And sometimes, how we respond defines everything that comes next.

My guest, , knows this intimately.

Fourteen years ago, Ron was a managing director at Barclays, building the Asian equity desk in the U.S., living the life he’d planned since college. He was an avid cyclist and triathlete, a husband, and father to three daughters. Then, on a seemingly ordinary Saturday after Thanksgiving, a driver fell asleep at the wheel and changed everything.

Ron woke up from a coma weeks later, paralyzed from the waist down, unable to speak, being told by his neurosurgeon that he would never walk again.

What struck me most when I first met Ron at our Wharton alumni networking group wasn’t his wheelchair. It was his warmth. Here was someone I’d expected to be one of the “sharks” from my Wall Street days, and instead I found someone profoundly human, funny, and present. Someone who had taken unimaginable disruption and somehow found a way forward.

This conversation isn’t about inspiration porn or making lemonade from lemons (Ron hates that phrase, by the way).

It’s about the messy, difficult, year-and-a-half-long process of accepting a new reality. It’s about finding purpose when your planned path disappears. And it’s about discovering that you’re far more powerful than you think—while also learning to accept what simply is.

For leaders navigating any form of disruption (career transitions, health challenges, market upheavals, or personal reinvention), Ron’s story offers something rare: honest wisdom about resilience that doesn’t minimize the pain.

The Weight of “Why Me?”

When Ron came home after five months in hospitals and rehab, his house looked the same. But his study had become his bedroom because he could never climb the stairs to his actual bedroom again. He threw himself into physical recovery with the same intensity he’d brought to Wall Street, but the results weren’t coming. He wasn’t getting back to what he was.

For a year and a half, Ron kept asking, “Why me? Why me? Why me?”

Then his wife, Betsy, who had been “incredibly patient,” finally said: “Enough. Shit happens to people and it happened to you, but you’ve got a family. You’ve got three daughters. They’re growing up. They need you to be a father. I need you to be a husband.”

That moment became Ron’s inflection point.

“All right, I’m just going to run with it,” he told himself. “This isn’t the life I planned. That’s not the life I ever pictured. But it is the life I have. And it’s not over. And there are still things for me to do.”

Notice what Ron says:

“I don’t know that I ever fully accept it, but I did own it.”

There’s profound wisdom in that distinction. Acceptance and ownership aren’t the same thing. You can own your reality, take full responsibility for what comes next, without accepting that it’s okay or fair or what you wanted.

Ownership is about agency.
Acceptance can sometimes feel like surrender.

Your Action:
If you’re in the middle of a disruption that feels unfair or overwhelming, give yourself permission to separate acceptance from ownership.

You don’t have to be okay with what happened.
You don’t have to like it.
But you can still own what you do next.

Ask yourself: What would ownership look like for me right now, even if I’m not ready to accept this?

When the Path You Planned Disappears

Ron had wanted a career on Wall Street since college. He lived it, breathed it, thrived in it.

He was the most senior person on the Asian equity desk at Lehman Brothers when it went under in 2008, already a massive disruption. He navigated that, landing at Barclays with even more responsibility, building out their U.S. sales team for Asian equities, including Japan.

Then the accident. And in 2012, long before work-from-home was standard, Ron realized: “I can’t do this.”

If there had been remote work options, he says, “everything would have been different.”

He could have managed the 2 a.m. calls to Asia. But the daily routine—getting into the office before 7 a.m., traveling to Boston every other week, the whole physical infrastructure of that life—was impossible now.

“Just like my whole routine, everything takes so much longer.”

The career he’d built for decades was gone.

But Ron didn’t stay stuck in that loss. Instead, he found himself exposed to a different problem: the home care system.

When he needed caregivers himself, he was shocked by the limited options. Either expensive agencies that gave you no choice in who showed up, or finding someone on your own, with no way to properly vet them.

“All these marketplace companies were forming, connecting buyers and providers online,” Ron remembered. “And we thought, well, why can’t we do something similar?”

That became Lean On We, a business that has now helped over 2,000 families in the greater New York area get better, more affordable care.

Ron couldn’t go back to Wall Street, but he found a way to have “a big impact on people in a more visceral way than I had previously.”

Your Action:
When your planned path disappears, look for the problems only you can see from your new vantage point.
Ron’s accident gave him lived experience with a broken system.

Your disruption—whatever it is—has likely exposed you to challenges, needs, or opportunities that others can’t see.

What problem are you now uniquely positioned to solve?

The Power of People Who Still See You

One detail from Ron’s story stuck with me: his network didn’t disappear when his mobility did.

In fact, they didn’t just support him, they helped him carve out a new path.

A former client who became president of a liberal arts school in Illinois invited Ron to be their commencement speaker.

Ron’s initial reaction? “I don’t know. I don’t know if I could do that. That’s a lot of work.”
But then he told himself: “If you don’t do it, you’re going to regret it.”

He went. His whole family came. Nearly 2,000 people heard him speak about living forward. “It was such an empowering experience,” he said.

A close childhood friend kept encouraging him to write and speak more:
“People want to hear from you. People are curious. People don’t know what life is like for somebody who’s paralyzed... You’re a manifestation that life isn’t over. And hearing from someone like you can make them think differently about their own challenges.”

These weren’t empty platitudes. These were people who still saw Ron—not as someone broken or diminished, but as someone with something valuable to offer.

They invited him to try something new. They pointed him in different directions. They believed in him when he was still figuring out how to believe in himself.

“I realized that I found writing meaningful,” Ron said, “sharing what I’m going through, partially for myself and partially because I could see that it had an impact on others as well.”

Now Ron is a keynote speaker, has built a growing newsletter, and is in the process of writing his first book. All because the people he impacted in his career and life needed him… in a new way.

Your Action:
Inventory your network not for what people can do for you, but for who still sees you clearly.

Who invites you to stretch?
Who points you toward new possibilities?
Who believes you have value to offer even when you’re not sure yourself?

Reach out to one of those people this week and tell them what their belief in you has meant.

Grit Without Delusion: The G.O.L.D. Standard

Ron has distilled his framework for resilience into something he calls “The New Gold Standard”—a nod both to his last name and his Wall Street career. It stands for:

• Grit

• Opportunity

• Learning

• Drive

The model came from what he’s learned since 2012 — since he took ownership of his new life. But what makes Ron’s approach different from typical resilience narratives is his refusal to traffic in false hope.

A couple of years ago, he tried an exoskeleton called ReWalk. Everyone was excited: “You’re going to be able to walk! You’re going to be able to do this and do that!”

But it hurt his shoulder, and more fundamentally, it wasn’t practical. Even in the best case, all it could do was let him walk in a park. “It wouldn’t have changed my life. I couldn’t get in this thing and get in the car and drive somewhere.”

It was like many of the other developments in spinal cord injury research that Ron has monitored. Yes, there have been exciting breakthroughs. But many of them help people with quadriplegia first—those without use of their hands and arms.

“Here I am watching with bated breath these developments, and then it’s a little bit like a mirage. I’m happy for these people who are going to be able to get this, but it’s not going to happen to me.”

There’s internal conflict in that: being genuinely happy for others while accepting that the help isn’t coming for you yet. “I’m disappointed, but I’m happy for people. And I’m just hoping that the next shoe will drop.”

This is the paradox Ron lives:
“I don’t think I have limiting beliefs. But I’m also realistic enough to know that some things aren’t possible.”

I’m consistently in awe of what Ron chooses to accomplish:

He’s run five marathons in a hand cycle.
He drives with hand controls—left thumb for gas, left hand for brake.
Getting into his car requires taking off one wheel, flipping the chair, taking off the other wheel, lifting the body over himself onto the passenger seat. “And that’s before I even leave the driveway.”

When I see Ron at our networking events, he always says, “I got it, I got it” even when I or others offer help. He does. But I also witness how much harder everything is.

Ron doesn’t deny the hard. He has simply figured out a way to live with it and through it.

Your Action:
Practice Ron’s paradox.

Challenge one limiting belief you hold about yourself or your situation:
What would you attempt if you truly believed you were “so much more powerful than you think”?

Simultaneously, identify one area where you’ve been holding onto false hope or unrealistic expectations:
What would change if you accepted that particular reality while still maintaining your agency everywhere else?

What Ron Would Tell His Younger Self

Near the end of our conversation, I asked Ron what he would tell his younger self. His answer surprised me:

“You are much more powerful than you think you are. The clichés that people have—some of them I think are terrible—but the idea that if you really put your mind to it, you can do a lot, you can do so much more than you think, that kind of cliché is true.”

Then he said something that I surprised me:

“I’m much more driven and much more purposeful now than I ever was. And I feel if I had been able to take this drive that I have now—that I so urgently need because I just need to work so much harder to get things done—if I had been able to bring that to bear earlier, I could have done different things.”

Read that again.

Ron is more driven now—in a wheelchair, navigating a world built for people who can walk—than he was as a high-performing managing director on Wall Street.

Why? Because necessity revealed capacity he didn’t know he had.

Most of us won’t access that level of drive until we’re forced to. But what if we didn’t wait? What if we took seriously the idea that we’re capable of far more than we currently believe?

Ron also clarified which clichés he hates. When people tell him he’s “taken sour lemons and made sweet lemonade,” he bristles:

“Really? Did I? I’m still in this wheelchair, by the way. That sour lemon still exists. I’m getting whatever juice I can out of it.”

Those platitudes, he says, “are meant to make people feel better, that this guy’s all right. You don’t have to worry about him. He’s got his act together.”

But he doesn’t need us to feel better. He needs us to understand that resilience isn’t about making everything okay. It’s about fortitude and perseverance in the face of things that remain decidedly not okay.

Your Action:
Don’t wait for a crisis to discover your full capacity.
Identify one area where you’ve been playing smaller than necessary—not because you lack ability, but because you haven’t urgently needed to show up bigger.

What would change if you brought Ron’s level of purposeful drive to that area starting now?

Moving Forward

Ron is working on a memoir. He’s focused on speaking, particularly to financial services audiences, the world he came from. He wants to share his perspective with young analysts and associates, with financial advisors who create wealth and independence for their clients but might not fully appreciate the importance of their work, and with leaders who want to create cultures where their people can reach their full potential.

“These are the sorts of messages that I can bestow on others,” he says.

He’s also continuing to build Lean On We, helping families navigate one of the most difficult transitions in life: caring for aging parents or managing their own care needs.

And he keeps showing up. At networking events. In the New York City Marathon (five times in a hand cycle). On Substack (Ron’s Ramblings) and LinkedIn. Doing the work.

When I watch Ron arrive at our gatherings, transferring from his car, navigating spaces designed for standing people, serving himself food while everyone else towers above him, I see someone living the truth he discovered:

• You’re more powerful than you think

• Your life isn’t over when your plan disappears

• Ownership matters more than acceptance

The world has a habit of telling people in wheelchairs that their lives are tragic, diminished, over. Ron’s existence is a quiet rebellion against that narrative.

Not because everything is fine—it’s not.

But because he decided that even in a life he never planned, never wanted, never asked for, there are still things for him to do.

And he’s doing them.

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Conversation Timestamps

[00:00 - 07:11] Introduction & The Accident

• Technical difficulties set the stage for our theme: disruption to reinvention

• Ron’s background: Managing Director at Barclays, building Asian equity desk

• The cycling accident: “She falls asleep, crosses the center line, and heads right at my buddy Zach and me”

• Waking up from a coma weeks later, paralyzed, unable to speak

• Ron’s reflection on showing his wheelchair on video calls

[07:11 - 16:27] The Lehman Brothers Collapse & Career Before the Accident

• Ron’s experience during Lehman’s collapse in 2008

• The cash advance story: trusting his instincts when talking points didn’t match reality

• His role selling Asian equities to U.S. institutions during Asia’s growth period

• What it meant to be on the equity desk covering China, Taiwan, Singapore, Hong Kong, Japan

• 50-mile cycling rides and physical fitness before the accident

[16:27 - 24:00] The Hospital, Rehab & Coming Home

• Two months in ICU, three months at Kessler Rehab

• The mental challenge of rehab: “No longer about healing you... it’s about teaching you how to live that life as a paraplegic”

• Coming home to a house that looked the same but wasn’t: the study became his bedroom

• The year and a half of asking “Why me?”

• Betsy’s intervention: “Enough. Shit happens to people and it happened to you, but you’ve got a family”

• Ron’s inflection point: “I don’t know that I ever fully accept it, but I did own it”

[24:00 - 30:00] The Birth of Lean On We

• Realizing he couldn’t return to his Wall Street career (pre-remote work era)

• Being exposed to the broken home care system as a patient

• The two inadequate options: expensive agencies with no choice, or DIY with no vetting

• Creating Lean On We as a marketplace connecting families with caregivers

• Helping over 2,000 families in the greater New York area

• The caregiver shortage crisis and immigration issues

• Empowering caregivers through direct relationships

[30:00 - 37:06] Global Perspective & Human Connection

• Ron’s memories of working with people in Hong Kong, Taiwan, Singapore

• The story of Jimmy Lai: from immigrant to billionaire to imprisoned activist

• “A guy who’s a billionaire could walk away and chose to be a symbol of everything that American values are supposed to be”

• Ron’s attempt to convince his family to move to Hong Kong

• The importance of building relationships across cultures

[37:06 - 44:56] Finding Purpose Through Writing & Speaking

• The TEDx talk opportunity

• Being invited to give a commencement speech at a liberal arts college in Illinois

• A childhood friend encouraging him to share his story more widely

• People’s misconceptions about life in a wheelchair

• The power of showing what’s possible: “If this guy in a wheelchair can do things, that is a mindset shift”

• Processing the word “inspiring”: “I’m just trying to live my life the best way I can”

• Ron’s relationship with technology and social media: bringing out the good in connectivity

[44:56 - 51:34] The New Gold Standard & What’s Next

• Ron’s framework: Grit, Opportunity, Learning, Drive

• Five New York City marathons in a hand cycle

• Working on a memoir and other books

• Focus on speaking to financial services audiences

• The importance of financial advisors’ work: “creating some sort of independence so people can go and live their dream”

• What Ron would tell his younger self: “You are much more powerful than you think you are”

• Being more driven now than ever before

• The clichés Ron hates: “You’ve taken your sour lemons and made sweet lemonade”

[51:34 - 57:50] Limiting Beliefs vs. Reality

• “I don’t think I have limiting beliefs. But I’m also realistic enough to know that some things aren’t possible”

• The exoskeleton experiment that didn’t work out

• Watching spinal cord injury research with hope and disappointment

• The mirage of breakthroughs that help others first

• Accepting what is while hoping for what might be

• The pairing of power and acceptance

• How to connect with Ron: LinkedIn, Substack (Ron’s Ramblings), rongold.live, and Lean On We

If Ron’s story resonates with you, you can find him on LinkedIn, read his Substack “Ron’s Ramblings,” visit his website at rongold.live, or learn more about Lean On We. And if you know financial services organizations looking for a speaker who brings real perspective on resilience, reinvention, and what actually matters, Ron is your person.

Share this post with leader who needs to learn more about the G.O.L.D. standard.

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What disruption are you navigating right now?
And what would it mean to own it, even if you’re not ready to accept it?

I’d love to hear from you—just hit reply or share a comment.

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May you lead without limits,

Hi there! 👋 Welcome to Lead without Limits, where I share weekly, actionable mini-guides based on real human experience (not theories and platitudes) to level up your leadership and career and feel more fulfilled in the process.

Only about 50% of employees strongly agree that they know what is expected of them at work, according to Gallup1.

(sigh) Unfortunately, that’s not surprising.

Even in a board game, where there are clear rules and objectives, there are a variety of ways to win (or lose).

In business, how you execute can be even more varied because the rules aren’t standardized, teams aren’t uniform, and the playing field is ever-changing.

Leaders know this, and yet, few give their team enough (or any) direction on what good is, and then get disappointed (and surprised) when their team misses the mark.

Their excuses are plentiful:

• “I’m too busy. I don’t have time.”

• “My team should know what I want.”

• “My expectations should be obvious.”

And the resulting problems multiply even faster:

• Wasted time because work has to be repeated

• Frustration from the leader, and from their team

• Missed or poor outcomes that lead to missed goals

• Top talent departing when they don’t see any improvement

It doesn’t have to be this way.

You can help your team deliver and make the process less difficult for them by setting up clear and effective expectations. Here’s how:

How to Set Expectations Well

The steps aren’t complicated, but each one has a purpose, and if you cut corners, you won’t maximize the opportunity.

When we lead well, the short-term benefits are only part of the picture. The long-term value is where the real payoff lies: a higher-performing team, developing leaders who can compound their results, and creating greater trust that will result in career-lasting relationships.

1. Set Aside Time

You can’t do the work if you haven’t given yourself the time to tackle it. And if this feels like a difficult task, all the more reason to set aside more time not less. Ideally, you set aside time weekly and monthly to accomplish the rest of the steps.

Take Action: I recommend at least 30 min weekly to reflect and to plan for adjustments the following week. In the future, you can reduce to 15 min. Monthly, set aside another 30 min to review your notes and adjust for the next month.

2. Assess & Don’t Assume

The issue to address and the one that trips up leaders most often is making assumptions about their team that they haven’t verified. Instead of assuming, assess actual data, observe behaviors, and ask your team.

• If you think your team is following all the steps, review their approach.

• If you think your team is collaborating well, ask others.

• If you think your guidance is clear, ask them.

Hope is nice in theory, but terrible in practice.

Take Action: Identify the areas where you have most concern and where there is the highest impact to the business. Then choose one thing to verify each week. You might find that this habit becomes easier over time and you can do more than one, but start with just one. And if you need to slow it down to one a month because of the complexity or scale of impact, fantastic. Quantity isn’t the goal. Impact is.

3. Prioritize & Tailor

You can’t and shouldn’t define everything. Focus on what’s most important and where your team needs the most guidance (e.g. a team that’s great at the technical elements, but isn’t savvy on people dynamics needs more guidance there and vice versa for the opposite skillset).

Take Action: Once you have identified the highest impact areas and verified where you team needs more guidance, assess where your team is strong and where it isn’t. Share more detail, offer examples, create group working sessions for when they need more help. Do the opposite in areas where they are already in a good place. This way, you’ll help them understand where they need to shore up their work and model how to do so.

4. Separate the What from the How and the Why

There are 3 different parts to setting expectations:

1. What is required: the outcomes, the results.

2. How it needs to be accomplished

3. Why is it important

When you communicate your expectations, be sure to distinguish each. The Why and the What always matter — don’t skimp on those. The How doesn’t always matter, but if you have boundaries or certain organizational norms you need your team to follow, don’t be mysterious — tell them.

By being clear on all three, your team will have more understanding of your specific expectations, but also how to anticipate your thinking going forward. It’s as if you’re giving them the algorithm in your head on how you set expectations. This is how great teams move fast and seamlessly.

Take Action: Setting expectations isn’t a complicated formula. Write down your What, How and Why before you connect with your team. Not sure if you’re being clear enough, prompt AI to ask you questions to clarify what you share.

5. Use Scenarios

Scenarios is one of the most underutilized managerial tool. They can help you communicate more nuance, give you insight into how your team thinks, and be an excellent tool to align with your team. As a bonus, they will get your team more engaged by creating a dialogue vs a one-way conversation.

Take Action: For each of the priority areas where you’ve identified that your expectations setting could be improved, imagine 1-3 scenarios that can help illuminate the What, How and/or Why. Bring one to your team in a test-run and explain what you’re trying to do. If everyone walks away more clear, then you have a win. If people aren’t feeling more aligned, then try another one. Have patience with this one. It might take a few run.

6. Group Discussions Scale Learning

For all of the above steps, you can do them 1:1 or in a group. Take advantage of opportunities to do these steps as a group when you can. It not only reduces the number of conversations you’ll need to have, your team will benefit from observing how each other engages and how they are making sense of what you share.

Tailoring your approach to what people on your team need will determine which path you take and when. It’s OK to go slower when someone needs more individual attention or more relationship building to create trust. And when possible, leverage the power of the group.

Take Action: As you identify which expectations need your focus, think about when you can bring those conversations (verification moments, scenario discussions, etc) into a group meeting. Normalizing these won’t just help with expectations setting, it reinforce a open and collaborative mindset that will improve how your team works overall.

7. Verify Your Progress

Pause regularly to verify what’s needed, the quality of your guidance, and level of understanding. Unfortunately, there is no GPS telling you if you’re moving in the right direction. You have to do the work to find out if you’re heading in the right direction or if you need to course correct.

Take Action: Ask your team, ask their collaborators, check your team’s results, and reflect on your observations. These are all signals to help you make sense of your progress. This is technically part of step one and two, and so if you’re setting aside 30 min every week to do this, you’ll be far less likely to miss anything.

8. Periodically Revisit & Adjust

Treat expectations as an ongoing exercise vs. a set of edicts set in stone. There are too many changes happening too rapidly to assume what you’ve designed at the start of an initiative will still hold true several weeks later. It might, but it’s smarter to design your approach as if it won’t.

Take Action: Make sure your team knows that your expectations will be dynamic based on business context and what you all learn as you go. This way, they won’t be surprised when you make adjustments. It also invites them to come to you if they see changes that should inform any changes. This way, it’s not just about what you know, but it’s what your entire team is learning along the way.

The best part of getting this right?

You can rinse and repeat and the work you do once compounds. Your team more deeply understands not just what you want, but how and why. They will also be able to cascade your expectations to more people — direct reports, collaborators, and even external partners. This will give you leverage and create greater cohesion.

It can feel like a significant time investment because it is. But remember, like all smart investments, this up-front investment will generate significant returns. Over time, if you’re working with the same people, you will have less to align on because you’ve done the alignment work already and if you’re onboarding new people, your extended team can help you translate these into practice and you won’t have to be only standard bearer.

Don’t wait. Get started this week: Choose one important initiative and one team member to work with. And start to set aside the time to plant the seeds now for far better results going forward.

I’ll be cheering you on!

May you lead without limits,

P.S. SAVE THE DATE: My next Substack Live is scheduled for this Friday, January 23rd at 2:30pm ET with Ron Gold. You don’t want to miss this conversation on resilience and what it means to redefine success. Link to come soon!

If you found today’s post helpful, the greatest thank you can give me is sharing it with another leader who might benefit. Thank you!

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And if you would be open to sharing how you have set excellent expectations with your team, I’d love to learn more.

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This piece captures my recent Substack Live conversation with Tom Hardin, the former FBI informant known as Tipper X. You can watch the full video above, read the article below, or jump to the timestamp summary at the end to find the moments that matter most to you.

The $46,000 Decision That Changed Everything

What’s the price of a career built over years of hard work and education? For Tom Hardin, it was $46,000.

Not millions. Not even hundreds of thousands. Forty-six thousand dollars in personal gain from four small insider trades that added just 1% to his hedge fund’s performance.

When I first met Tom two years ago at a local networking event, and he introduced himself as “a former FBI informant,” I’ll be honest, I had no idea what that even meant.

What I’ve learned since has fundamentally changed how I think about ethical decision-making in leadership.

Tom’s story isn’t about a bad person doing bad things. It’s about a good person, Wharton-educated, hardworking, from a middle-class Atlanta family, who made four decisions in isolation that derailed his entire career at age 29. He then became the FBI’s top informant (codenamed Tipper X) in the largest insider trading investigation in history, spending two years wearing a wire to help take down corruption on Wall Street.

His upcoming book (Wired on Wall Street), launching February 25th, chronicles this journey. But our recent Substack Live conversation revealed something more important than the dramatic tale of espionage and courtroom drama: the anatomy of how ethical lines get crossed, and what leaders can do to prevent it.

Because here’s what struck me most: Tom’s experience is a cautionary tale for every leader navigating ambiguous situations under pressure. The kind of pressure we’re all facing right now: to grow faster, cut costs, hit quarterly numbers, stay ahead of AI disruption, do more with less.

Here’s what I learned.

Theme 1: The Slippery Slope Starts Long Before the Line is Crossed

Tom didn’t wake up one day and decide to commit securities fraud. The groundwork was laid years earlier.

Insider trading was “an open secret.” Everyone knew. Hedge funds would have value-added investors who worked at public companies call them with inside information. Or they’d hire analysts from tech companies specifically to call back for tips from their former colleagues.

Tom knew this was happening. And like many of us when we see problematic behavior around us, he told himself: “That’s happening, but it’s not my world. I don’t have those kinds of contacts. It wouldn’t be me.”

The critical mistake? He never asked himself: “If I were in that position one day, what would I do?”

There was no pre-mortem. No mental rehearsal. No conversation with a mentor about the ethical dilemmas he was witnessing. He simply put it out of his mind and went back to the intellectual work he loved—analyzing market trends, debating stock positions, building investment theses.

Then his boss came to him after a bad quarter and said: “We need to make money every month, Tom, or we aren’t going to survive. We have to start looking for shorter-term opportunities.”

Ambiguous. Pressurizing. Open to interpretation.

Tom didn’t ask clarifying questions. Are we talking about doing what everybody else is doing? Are we staying within legal and ethical guardrails?

Within months, a tip landed in his lap. Then another. And because he’d never mentally prepared for that moment, he rationalized: These other guys are going to make millions. I’ll just buy a small amount. Who am I hurting? It’s just one trade. I’m still a good person.

Action for Leaders:

Don’t wait for the ethical dilemma to arrive.
Create space now—in team meetings, in one-on-ones, in your own reflection time—to discuss the gray areas you’re witnessing in your industry. Ask yourself and your team: “If we were in that situation, what would we do?” Make the discussion discussable before the pressure is on.

Theme 2: Ambiguity Is the Enemy of Ethics

When I asked Tom what could have prevented those initial trades, his answer was immediate: clarity and conversation.

His boss’s directive—”we need to make money every month”—was the textbook definition of ambiguous leadership communication. And as Tom now tells companies around the world:

“Ambiguity is the enemy of ethics and integrity.”

Here’s how the dangerous pattern unfolds:

1. Leaders send ambiguous messages (”We have to hit this number” / “Do whatever it takes” / “I don’t want to know the details”)

2. Teams pretend the message wasn’t ambiguous (nobody asks clarifying questions for fear of looking difficult)

3. The ambiguity becomes undiscussable (”Are you questioning my communication? You know what I mean, just get it done”)

4. The undiscussability becomes undiscussable (culture of silence is established)

This is how you end up with values on the wall that don’t match the behavior in the halls.

Tom described visiting companies for compliance training where young employees pull him aside afterward and say:

“Yeah, what they say on the wall about speaking up? We would never do that here. If we raise our hand, we’ll never hear back and then we’re worried about our jobs.”

The fraud triangle that explains why employees cross ethical lines requires three elements:

1. Perceived need (pressure to perform)

2. Opportunity (lack of controls—in Tom’s case, he could buy stocks under 1% of assets without approval)

3. Rationalization (self-exception by reasoning—”I’m a good person, this is just once, it’s a small amount”)

But here’s what struck me: All three of these elements are amplified by ambiguous leadership communication.

Action for Leaders:

Audit your recent communications to your team. Where have you been ambiguous—perhaps intentionally—about how to achieve goals? Where might your team be interpreting “do whatever it takes” as permission to bend rules? Schedule a conversation specifically to clarify: What are we willing to do? What are we absolutely not willing to do? Make it safe to ask these questions.

Theme 3: Isolation Accelerates Poor Decisions

One of the most haunting moments in our conversation was when Tom said:

“If I had been talking to somebody outside my firm, outside my industry, maybe a mentor, and said, ‘Hey, you won’t believe what’s happening. These guys are making millions. I just got this tip. I’m thinking about taking a small trade just to play along...’ Certainly anybody on this call, if you’re my mentor, you would have slapped young Tom around.”

But he didn’t have that conversation.

He made the decision in isolation. And in isolation, it was very easy to do his own mental gymnastics: I’m a good guy. I’m a faithful husband. I go to church. I make thousands of trades a year. I can make four bad ones. They’re small. Who cares?

Tom told me:

“It would have been very hard to do that if I just jumped outside my head.”

This resonated deeply with me.

How many of us, when facing a difficult decision, keep it entirely in our own heads? We tell ourselves we’re being thoughtful, strategic, protecting confidentiality. But sometimes we’re just protecting ourselves from accountability.

After the FBI approached him, Tom could only tell his wife. For two years, he wore a wire, building cases against other traders, while maintaining his day job and his cover. He was juggling multiple, challenging identities: former trader, FBI informant, stay-at-home dad after he left his firm, ultramarathon runner.

But even after his name came out as Tipper X, even after sentencing, Tom said:

“I was so focused on myself. I hate to say it, I wasn’t really considering what my wife was going through.”

It wasn’t until he started volunteering at his church, getting outside his own head by helping others, that he began to heal. And it wasn’t until he was interviewed for his book that he finally asked his wife: “What was it like for you?”

Her response: “Thanks for asking, Tom, because you never did.”

Action for Leaders:

Build your “personal board of directors.” The 2-3 people outside your immediate team or company who you can call when you’re facing ambiguous decisions. Make it a practice to voice your dilemmas out loud, even (especially) when you think you have it figured out. The act of explaining your reasoning to someone else often reveals the flaws in your logic.

Note: Worried about confidentiality? Engage an attorney, have your confidants sign NDAs. Even when you get help, do it all above board.

Theme 4: Redemption Requires Radical Honesty and Service

When the FBI approached Tom on a Manhattan sidewalk at 6:30 AM on July 8, 2008, his first thought wasn’t about prison. It was: “Oh my gosh, my dad’s going to kill me.”

His father had worked for 40 years, commuting daily from their middle-class Atlanta suburb, so that Tom could have better opportunities. His mother had run a childcare business from their home. They had instilled in him a work ethic and drive to succeed that led him to read the entire World Book Encyclopedia when he was 8 (taking two years to get from “Akin to Zygote”) and eventually to Wharton.

And here he was, having thrown it all away.

His second thought:

“My wife’s going to leave. We just got married. She had no idea about the trades. She has every right to leave.”

But when he finally told her that Friday (after days of bed sweats and panic attacks), she said something remarkable: “You didn’t do anything to hurt me. And if they’re giving you a chance to clean up the industry, you should do it.”

Tom shared that 85% of marriages end in situations like this. His survived because of radical honesty and her extraordinary grace.

For two years, Tom worked as an FBI informant, meeting targets at Starbucks (he mentions it 15 times in his book, he laughed), trying to get them to admit to federal crimes. He was terrible at it initially—too eager to get to the punchline. The FBI would listen to recordings and say, “Tom, you’re doing a bad job. You have to be silent.”

There was no training at the FBI Academy for this. It was swim by being dumped in the deep end.

After his sentencing in 2015 (no prison time thanks to an FBI letter detailing his cooperation), he still had a felony conviction. He couldn’t get a job. His wife continued working while he became a stay-at-home dad.

He tried real estate deals (investors Googled him), drop-shipping on eBay (suppliers hijacked his listings). He volunteered at church, shipping clothes to Haiti. He ran ultra marathons to get fit and mentally heal, but it sometimes turned into a way to avoid difficult conversations with his wife about their financial reality.

Then he went on a podcast to tell his story. An FBI agent happened to be listening and called him: “Come talk to the FBI. What you discussed: the pressures, the dynamics, the rationalization. You could do a better job of compliance training for this industry.”

For a year, Tom emailed every business school in the New York area: “I’m Tipper X. I won’t charge for this. I’m just trying to get my reps.” A few schools let him in. Then a company asked: “How much do you charge?”

“$3,000?” he ventured.

He got paid. He told his wife: “You can quit your job.”

She replied: “Are you crazy? You just made $3,000. That’s it.”

But Tom said:

“When my family was at stake, when my wife had been so amazing, I knew I had to step up. I had to make this work. Whatever it was going to take.”

Ten years later, he speaks to Fortune 500 companies around the world. His first book launches February 25th. And his definition of success has completely transformed.

“It’s not about chasing status anymore,” he told me. “Success for me is more about special moments than outcomes. If somebody can pick up this book who knows nothing about finance or Wall Street, and maybe they’re going through a terrible, maybe self-inflicted situation in their own lives and can pull a few nuggets from this experience to help them—that’s what matters.”

Action for Leaders:

When things go wrong, whether through your own mistakes or your team’s, resist the instinct to minimize, rationalize, or hide. Radical honesty, even when it’s painful, is the only path to genuine redemption and rebuilt trust. And consider: How can you transform your hardest experiences into service to others?

One Question That Changes Everything

Near the end of our conversation, Tom shared something that crystallized all of these themes.

He’s read countless corporate codes of conduct, those documents we all sign (but very few actually read) annually with 10 philosophical questions to ask ourselves before making a decision.

At one European company, he asked if he could rip up their 10-question checklist on stage.

“Could you just ask yourself one question?” he proposed. “If I make this decision, am I willing to be held accountable for this decision at the end of the day?“

That’s it. Not five philosophical questions from your college ethics class. Just that one.

“If you can answer that,” Tom said, “you’re pretty much on the right path.”

Why This Matters Now

Tom’s story happened during the 2008 financial crisis, a time when the entire financial world was collapsing, when institutions that were never supposed to be wobbly were literally crumbling.

Sound familiar?

We’re living through our own period of unprecedented disruption. AI is transforming how we work. Economic uncertainty is putting pressure on every leader to deliver results. The temptation to take shortcuts, to be ambiguous about how we achieve goals, to look the other way when we see problematic behavior, to make decisions in isolation, has never been stronger.

Tom’s journey from rising hedge fund trader to FBI informant to keynote speaker and author isn’t just a dramatic story. It’s a mirror showing us what happens when good people face pressure without preparation, when ambiguity fills the space where clarity should be, when isolation replaces conversation.

The good news? Every single one of the risk factors Tom faced is preventable. Not easy to prevent, but possible.

It starts with having the conversations before the pressure arrives. With making ambiguity discussable. With building your board of directors. With asking yourself that one critical question.

Tom made four bad choices at 29. But he made one very good choice: he married his wife Sue. And through radical honesty, service to others, and a complete redefinition of success, he’s built a second career helping leaders avoid the mistakes he made.

His story reminds us that redemption is possible. But prevention is better.

Get the Book

Tom’s book launches February 25th. Companies ordering 10 or more copies will receive supplemental discussion materials around ethics decision-making.

Visit tipperx.com/book to pre-order (pre-orders in the next six weeks help move the algorithms during publication week).

You can also find Tom on Substack at tipperx.substack.com and on LinkedIn under Tipper X.

Conversation Timestamps

Want to dive deeper into specific parts of our conversation? Here’s your guide:

[00:00 - 04:04] Introduction and Tom’s background growing up in Atlanta

[04:05 - 08:05] The Wharton experience and dealing with imposter syndrome

[08:06 - 12:16] Landing the coveted hedge fund job and the tech bubble

[12:17 - 17:09] Becoming aware of insider trading as an “open secret”

[17:10 - 23:38] The moment of crossing the line: receiving the tip and placing the first trade

[23:39 - 28:02] The FBI approach on a Manhattan sidewalk

[28:03 - 33:03] Telling his wife and becoming an informant

[33:04 - 37:57] Two years wearing a wire and the Tipper X reveal

[37:58 - 45:00] The dark years: stay-at-home dad, ultra marathons, and finding purpose through service

[45:01 - 50:02] Sentencing, starting the speaking business, and writing the book

[50:03 - 55:10] What could have prevented it: lessons for leaders on ambiguity and organizational culture

[55:11 - 57:55] Closing thoughts on success, accountability, and the one question that changes everything

Thanks for reading Lead Without Limits. If you found value in this conversation, please share it with a leader who needs to hear Tom’s story. And if you’re facing an ambiguous situation right now, I’d love to hear about it. Sometimes we all need someone to help us jump outside our own heads.

May you lead without limits,

Hi there! Welcome to Lead without Limits, where I share weekly, actionable mini-guides based on real human experience (not theories and platitudes) to level up your leadership and career and feel more fulfilled in the process.

Whew! (*sigh*)

We’re on the other side of the end-of-year. A time that looks sparkly and festive on the outside, but actually drives most leaders bonkers with stress.

Budget negotiations, goal-setting machinations, end-of-year performance reviews, team celebrations, all while pushing to hit your annual targets — it’s no wonder leaders leave the season often feeling relief more than joy.

Perhaps one of the biggest drivers of stress is the feeling that you didn’t do enough, didn’t achieve enough, didn’t grow enough. This is often coupled with a stifling feeling masquerading as false optimism that this next year will be “better.”

You’ll hit higher targets, make more money, create more value — be more.

I don’t know about you, but that constant refrain of MORE starts off like an anthem but can, over time, devolve into the drumbeat of a death march.

What if this next year isn’t the year of more?

What if it’s the year of clarity, focus, and intentional subtraction?

What if it’s the year of less?

Every time I gave myself permission to choose “less”, I achieved more.

I confess, I love more. I grew up feeling in my bones that I needed more. More clothes, more friends, more travel, more food. It wasn’t that I didn’t have enough. I did. I just wanted more.

It wasn’t until I had achieved what was billed to me as the top of the job hierarchy after college (Tech investment banking on Sand Hill Road in 2001 — if you know, you know) that I realized that more on everyone else’s terms didn’t work for me.

More hours of work, more multi-million dollar deals, more late nights, more business trips — they not only didn’t match my interests, I tortured my body to force myself to do them. The more it felt bad, the harder I pushed.

Only when I left the finance world and started to work in client success for a small technology start-up, did I realize how choosing “less” could lead so much more.

It happened over and over in my career:

• Leaving a role at a 1000+ person, dysfunctional startup while 6-months pregnant to join a 10-person joint-venture because I was an after-thought in the first vs. an essential leader in the second.

  • Result: I helped launch a grow a $50M business and ultimately became CEO.

• Choosing to take a non-CEO role after my first stint as CEO because I wanted to work with people I trusted and needed health insurance to grow our family (infertility treatments are expensive).

  • Result: I made lifelong work friendships and my daughter was born 9 months later.

• Leaving corporate America in my mid-40s, at the supposed height of my executive career potential, to pursue my 20+ year dream of becoming a coach and artist.

  • Result: I get to spend my days doing everything I’ve longed to do with full autonomy and more creative energy than I’ve ever experienced in my life.

These decisions weren’t all roses and sunshine. But the end result was the same: By getting clear on what I was willing to deprioritize, I was able to make room for what actually mattered to me.

The most surprising outcome?

Once I made the decision on what mattered and what I was willing to let go, everything else flowed nearly seamlessly. What caught me even more off guard was that I was rewarded with far more than what I was seeking.

You can do it, too.
Here’s how.

Step 1: Look Further Ahead Than One Year

Start with visualizing where you want to be 1-2+ years from now.

Ask yourself:

• Who are you in this future moment?

• What matters to you?

• How do you feel?

Don’t overthink it. Trust your initial reactions. Jot it down. We’ll reflect on it in a moment.

Why that far out? Because real change takes real time. Even if you know this is a thought exercise, your brain is going to try to rationalize a response. Don’t. Use the distance to help you escape your current context and the short-term noise.

Step 2: Set Goals — and Anti-Goals

Using your vision as a guide, start to create a map of how you’ll get there.

Make 2 lists:

• Goals: What needs to happen to make your vision a reality

• Anti-Goals: What cannot to happen — this is what you’re intentionally deprioritizing

Don’t worry about timing or too many specifics just yet. This is meant to be a broad outline for now.

Both lists matter. The first tells you where you can focus your attention. The second helps you create freedom and space to maintain that focus without guilt and with more energy.

You know you’ve the exercise well when the first list makes you feel excitement (and maybe a few nerves, the worthy stuff usually does). And the second list should make you feel relief that you get to let some things go.

Step 3: Less Is Not Laziness — It’s Precision

This next step is a mindset shift.

You need it because you are rewiring deep programming. Even if part of you believes that less is more, more of you will still default to “more is more” as the answer.

Change requires repetition. Every day, schedule 5 min to remind yourself:

• Focus as a leadership advantage

• How fewer priorities create momentum

• Less rushing means more presence, more joy

Adjust the words to make them your own, put them on post-it’s, or use them as a meditation mantra. It doesn’t matter the specific method, it matters that you commit to reiterating it to yourself intentionally and regularly.

You’ll know you’re on the right track when you start to see the shift as not just something that will benefit you, but something that will benefit your team and the people around you.

Step 4: Prioritize 1-3 Goals (or Anti-Goals)

OK, it’s time to translate your vision goals and anti-goals into no more than 1-3 areas of focus for this next year. Ideally, choose just 1 to get started.

Use these questions to help you:

• What is something you can see yourself doing / stop doing this week?

• What will noticeably move you towards your vision?

• What feels more easeful, more frictionless?

Don’t worry too much about choosing the right one. Even just focusing on one thing will be progress. Sometimes the only way to know is to experiment.

Remember, less is more.
It’ll feel like it’s not enough. It’ll feel uncomfortable. You’ll hear an inner voice that will chastise you and make you doubt yourself. That’s a sign you’re on the right track. Hold steady. Don’t give in.

As you make progress, you can reassess what’s next. I prefer 3-month planning cycles. Too much changes too quickly to go far beyond that.

Importantly, don’t feel pressure to add more. If after 3 months, you’re feeling progress, and there is more to do (or not do), and you’re seeing the positive effects, it’s OK to stay the course.

The progress you can make with a singular, consistent focus can be life-changing. Don’t be afraid to give yourself (and your team) the opportunity to experience the full power of less is more.

You can do it!

“The ability to simplify means to eliminate the unnecessary so that the necessary may speak.”
— Hans Hofmann

The first time I did this exercise, I was so consumed by fear of not doing it correctly, the entire point of the exercise was lost on me. But then I tried again, and it landed.

The point isn’t to gain perfect clarity. The point is to give yourself permission to prioritize what matters and let go of the rest.

If this resonated with you, but you’re not sure if you can give yourself the time to go through the full exercise, don’t make this harder than it has to be.

• Just choose one thing that feels obvious and truly matters.

• Or choose one thing that you know isn’t adding enough value or is drain on your energy.

Let one of these these become your goal or anti-goal.

You can do this. You need to do this.
A focused leader is a more strategic leader.

Do it for your future self. Do it for your team. Do it for the people you serve.

I’ll be cheering you on!

May you lead without limits,

P.S. SAVE THE DATE: My next Substack Live is scheduled for next Monday, January 12th at 3:30pm ET with , otherwise known as TipperX — the most prolific FBI informant in Wall Street history. You don’t want to miss this conversation on Spies, Lies, & Tragedy: How One Leader Survived & Thrived. Download the Substack app to join. (Event link)

Hi there! Welcome to Lead without Limits where I share weekly, actionable mini-guides based on real human experience (not theories and platitudes) to level up your leadership and career and feel more fulfilled in the process.

From tears and frustration to power and optimism.
From fear and trepidation to confidence and clarity.
From false urgency and exhaustion to rest and rejuvenation.

2025 was a year of observation for me.
I bore witness to so many leaders stepping up and stepping in.

These were not easy moments.
In many cases, these were some of the most difficult seasons to navigate in their careers, but they chose to face them with courage and resolve.

Here are the themes that I found myself gravitating towards as I close out this year and prepare for the next. I hope they inspire you as much as they inspired me:

Theme 1: After a Layoff, Speed Isn’t Strategy

After years of climbing up, pacing ahead of others, and reaching pinnacles not out of breath, but ready for more, a layoff doesn’t just feel like a setback. It can feel like a deathblow.

For highly successful leaders, the first time is often the hardest. Coupled with the current business context of tightening belts, AI euphoria/mayhem, and geopolitical unpredictability, it can feel like the cards are stacked high against you.

Money may feel like a legitimate reason to hurry, but your psychological state is far more important. Rush into a search when you aren’t in the right frame of mind, and you’ll just be treading water, or worse, making a negative impression.

I saw over and over again, the leaders who paused, gave themselves time to process and heal, were the ones who pulled out of the negativity spiral. Networking, interviews, and decisions came easier when they weren’t consumed by anger, regret, and shame.

One found a larger role where they aren’t just essential (they always have been), but they feel valued and valuable in a way that wasn’t present in their last organization.

Another found a role that was more senior, higher pay, and with greater influence at a fast-growing firm with high-profile clients.

Another found a consulting opportunity in a domain they never would have considered in the past, but has now found deep fulfillment.

Go deeper: For more, read my post on how to reclaim your power after a layoff. Share it with a friend who might need a reminder to take care.

Theme 2: Isolation Feels Productive — Until It Isn’t

Leadership roles are, by definition, isolating.

Between the confidential information, the difficult decisions, and the volume of responsibility, it isn’t easy to share what you’re going through. It’s no surprise that most leaders have a tiny circle of confidantes, and even those are often partitioned by content areas, leaving few people, if any, having a full picture of what you are experiencing and navigating.

But this way of working takes its toll over time. Whether you choose to hire people to provide the support you need (therapists, coaches, etc), or you build a “trusted circle,” of friends, even leaders need outlets.

This is particularly true if you are feeling stressed or even lost. Being vulnerable feels risky because it is. But retreating into yourself often won’t help you find your way through darker or more challenging times.

As I close out 2025, my clients who have built these circles are the ones that remind me to continue to do the same. My most difficult moments in my career weren’t just characterized by work issues, they were also the moments when I was most disconnected from friends and family.

Go deeper: If you’re finding that you are feeling alone, consider one relationship you could build or strengthen. Make a commitment to do so in the new year.

Theme 3: Even Leaders Need to Be Seen

Too many people buy into the myth that senior leaders are self-sustaining, all-knowing, and omnipresent. They don’t need external feedback or praise. They should just “know.”

Even as someone who has been CEO and COO, I fall into this trap of assuming that leaders are somehow superhuman and therefore don’t require (or deserve) human considerations.

But it’s just not true: Leaders need recognition, too.

Feeling this way is not a sign that you are a narcissist or weak. It’s also not a sign that your team doesn’t care or doesn’t want to share.

It’s a sign you need to design systems to help you get the feedback and acknowledgement you need.

Go deeper: Learn how to source the validation you need in this LinkedIn carousel post. Implement one of these systems, and you’ll not only get more feedback, but so will your team.

Theme 4: Relationships First, Transactions Second

When you are in a high-stakes conversation, it’s easy to get focused on the transactional outcome: should we hire the candidate, can I save a few thousand dollars on the contract, etc.

But that’s a mistake.

The deal or decision may matter in the moment, but the relationship you are building (or destroying) will matter far longer. Share what you are thinking, give the other person the benefit of the doubt, and work together to find the optimal outcome.

When you reframe the situation as an opportunity to collaborate vs. an adversarial encounter, the process doesn’t just lead to better outcomes, it means that you’ll be building trust at the same time. The transaction may not matter 5 years from now, but the relationship will.

Go deeper: For more on how to prioritize collaboration even in a negotiation, read this post about a leader who negotiated a complex compensation agreement and got exactly what she wanted by providing the context her hiring manager needed to make a case for her.

Theme 5: Changing Habits Isn’t Linear — and That’s Not Failure

“Growth is uncomfortable because you’ve never been here before.”
— Kristin Lohr

Successful leaders are used to high expectations achieved at a high pace. But when you are changing deeper wiring, progress takes longer, is harder to predict, and success isn’t a hockey stick to the right.

My first corporate client this year had that exact experience. A C-suite leader and his team signed up for the Positive Intelligence mindset program I offer alongside one-on-one coaching.

Even as some of the group made strides quickly initially, others struggled to get started. They are part of a fast-changing organization with big ambitious goals. It is easy to lose momentum when your days are filled with curveballs and one high stakes decision after another.

My guidance? When you are changing a habit, don’t expect to change your immediate reaction or instinct — they are wired deep. The win is simply becoming aware of your reaction and pausing to choose your next action.

Once you start to reframe success as progress, not perfection, new habits become easier to adopt. Stumbles no longer feel like setbacks. They become part of the muscle-building you need to hone your new skills.

Go deeper: Interested in strengthening your mindset. Start with taking the Positive Intelligence Saboteur Assessment. It’s free and only takes a few minutes and what it reveals might help you determine what habit or skill you want to focus on next year. And you can always ping me if you want to explore how to quiet your saboteurs.

Your Leadership is Needed Now More than Ever

The world is in desperate need of more leaders, who are skilled and truly care about the people and organizations they lead.

The themes above highlight how challenging it is to be a leader today. But they also point to how leaders must first take care of themselves before they can provide the kind of direction, decision-making, and determination that can build successful teams.

As we close out the year, take the time to capture your themes:

• What are some of the challenges you faced?

• What is giving you energy and resolve?

• What helped you grow this year?

• How do you want to direct your attention going forward?

I’d love to hear more in the Comments below or in a reply to my email. I read every one.

I wish you the very best and look forward to seeing you in the new year!

May you lead without limits,

Welcome to Lead without Limits, where I share weekly insights earned in the C-Suite: building businesses and teams, while creating a career worth savoring.

The end of year often feels like a mad-dash.

Between focusing on what you need to do for your team (hitting end-of-year targets, running annual reviews, and setting the strategy, goals, and budget for the next year) and your family (gift giving, travel plans, hosting, and more) there isn’t a moment to breathe.

Your calendar is intentionally overscheduled and overwhelming, trying to fit in all the pieces and still making room for magical moments.

“Agency is the capacity to act deliberately in the world.”
— Albert Bandura

In the sea of content telling you to buy more and do more, this post is the opposite. This holiday season, I want to give you permission to lead, choose, and live differently. Without apology.

The beauty of permission is that it’s yours to give.

The most ambitious, heart-led leaders are often the ones who forget their own agency the fastest. Between caring for your stakeholders (investors, customers, partners), and caring for your team, you load up your obligations faster than a child rips through Christmas present wrappings.

And yet the burden you place on yourself doesn’t have to be so heavy.

Each time I made a decision that was aligned with what I knew to be the right way forward, I didn’t just feel a weight come of my shoulders, I could feel momentum building in my energy and thinking.

When we stop doing things that are no longer feel right, and instead choose actions and paths that are in alignment with what we know would work better, that’s when we are leading with our full power.

Write yourself a permission slip that’s right for you.

Below are just a few examples of how you can gift yourself permission this holiday season. Choose one or several, whatever feels right to you. Don’t see one that works for you, write your own.

When you give yourself the permission slip(s) you need, you’ll close out the year with greater peace and enter the next year more replenished and ready to move forward.

1. Permission to slow down without falling behind

We only hear about the big wins and view the highlights reel, but almost every successful leader had a quiet season or several:

• Vera Wang: After failing to make the 1968 Olympic figure skating team and spending 15 years as a fashion editor, Wang did not enter the fashion industry as a designer until she was 40.

• Steve Jobs: Dropped out of college and spent a year traveling through India and meditating before returning to found Apple.

• Toni Morrison: She worked as an editor at Random House for years while raising two children as a single mother. She did not publish her first novel, The Bluest Eye, until she was 39, and it was not until she was 62 that she became the first African American woman to win the Nobel Prize for Literature.

• Stan Lee: The Marvel visionary spent 20 years in the comic book industry mostly failing and was ready to quit at age 38 before creating the Fantastic Four.

If your body or your heart is telling you you need a break, listen. Even if you can’t leave your current post, consider scaling back, setting new boundaries, and reorienting your time. Your future self is waiting for you to make space for them to emerge.

2. Permission to redefine success

“When a path no longer serves you, it is not disloyal to leave it.”
— Unknown

I left college with everyone else’s goals and dreams in mind but my own. I knew this. And yet I still took a role doing what left me drained and empty every day.

A year and a half later, when I finally decided (and my body screamed), I needed a change. Not just a different job, but a different company, a different industry, a different role.

Throughout my career, I did that over and over again. Even when the people around me told me I was making a mistake, choosing the wrong path, or leaving money on the table.

It’s your life. It’s your career. Do what feels right for you.
Don’t stay on a path just because it’s the one you’re on. No one else will have to look back on your life and wonder “what if?”

When you reflect on your decisions 20 years, 30 years, or even 40 years from now, how will you feel? Did you take the risks worth taking? Did you aim too low? Did you lead and live to your full potential?

The only person whose answers matter is you.
Pause this end of year and ask yourself, what does success mean to me now?

3. Permission to design an organization, role, or leadership style that fits you

Some leaders seem to have a job designed perfectly for them:
The responsibilities play to their strengths.
The schedule fits their routines.
The requirements fit into their life.

Their secret?
They designed it that way.
And you can, too.

Too many leaders create unnecessary restrictions around how they lead and run an organization. They assume that where they started, what they inherited, or their old habits must remain constant, as if they are calcified.

Some organizations are indeed difficult to change, and for sure, habits can take time, but too often the limitations you create in your head aren’t based in fact. They are based on fear.

What if this holiday season, you stopped listening to your fear and started listening to the vision you have for what you want?

Dream up the ideal role, organization, leadership style that you want to embody. Don’t hold back, don’t think small. Write it all down. You might be surprised how even putting it on paper will help you find ways to make it possible.

4. Permission to speak up — even when it feels inconvenient or uncomfortable

Even if you’ve been leading for years or decades, there are likely some topics, people, or situations that have you clamming up.

But when you shut down, you are doing yourself and your team a disservice:

• You’re giving in to your fear and letting it shrink you

• The people around you are deprived of your wisdom

• Issues that need addressing get pushed aside, delaying outcomes and creating risk

• You’re building a habit in your mind that self-reinforces and hurts you and your organization

Speaking up isn’t just for you. When you do so, especially when it doesn’t come easy, you’re modeling to the people around you that they can do the same.

Everyone benefits when there is a free-flowing exchange of ideas. Help yourself and your team build that type of culture by leading the way.

5. Permission to want more and less at the same time

As someone who is curious about everything and loves to support everyone, I often set annual intentions to do less. And yet, if I’m honest, I often still want more.

If this sounds like you, too, what if you didn’t have to choose? What if you can have both?

I just finished reading Amanda Goetz’s book Toxic Grit: How to Have It All and (Actually) Love What You Have. She shares her methodology called Character Theory. It’s a practical set of steps to make the statement, “you can have it all, just not all at once” possible. (I highly recommend it — it’s a great holiday gift!)

Even if you don’t have time to read Amanda’s book. You can take the most important concept and give yourself permission to want it all. You simply have to set seasons and moments for each element.

Don’t make the mistake of trying to cram everything in all at once. Pace yourself, and you might be surprised at what is possible, even in one year.

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Reflection questions to help you gift yourself the permission you need.

If you want more food for thought to help you choose the right permission slip(s), start with these reflection questions. They will give you insight into what matters most for you right now:

• What belief about success once protected you — but may now be limiting you?

• Who are three people you’d love to meet, even if it feels unrealistic today?

• What skill, if developed, would fundamentally change how you lead?

• What skill or habit once served you — but now quietly costs you?

• Where are you asking for permission from others instead of granting it to yourself?

What you need most is within.

As I reflect on what permission I need, I feel a pull to slow down next year. To hone my craft(s) and become more easeful in all that I do. It’s so easy to get swept up by the dopamine hits that come from social media and even hitting my goals.

But I know that even as I celebrate all the progress from this past year, I can make next year that much more rewarding and fun if I can strengthen my approach, smooth my process, and be patient as I hone my how.

I wish you a beautiful holiday season filled to the brim (if you want it to be) or quiet and peaceful (if that’s what feels right).

Thank you for being here, with me, on this journey to lead without limits.

Welcome to Lead without Limits where I share unvarnished truths and actionable tips each week to help you traverse the often difficult terrain of work and life with more joy and energy.

Last week, I had the privilege of hosting Molina-Shaefer for a Substack Live conversation that left me thinking bigger, dreaming bolder, and reconsidering what’s possible in my own career. Maia’s journey -- from boxing ring to combat zones, from military diplomat to nonprofit leader --offers a masterclass in navigating career transitions while staying anchored to your core purpose.

If you’ve ever stood at a career crossroads, wondered whether you’re “qualified enough” to make a leap, or struggled to maintain your identity through major transitions, this conversation is for you.

The Power of “Challenge Accepted”

Maia’s path to the Naval Academy didn’t follow the script she’d imagined. Despite being recruited for sports by multiple colleges and submitting what she thought was a strong application, she was rejected.

“It was a huge surprise and a shock to me when I actually didn’t get accepted. I wasn’t really used to being rejected or someone telling me, you’re not good enough to come to our school.”

Instead of internalizing that rejection, Maia used it as fuel. She spent an extra year at a foundation school, focusing on STEM courses, and reapplied. The second time, she got in.

Here’s what strikes me about this: Maia didn’t just persist blindly. She took that “no” as information. She identified what needed strengthening, invested the time to build those skills, and came back stronger.

Your Takeaway:
When you face rejection or a setback, ask yourself: Is this a hard stop, or is this feedback about what I need to develop? Sometimes the path to where you want to go requires a detour that actually makes you more prepared for what’s ahead.

Leading Through Listening

One of the most powerful themes in our conversation was Maia’s approach to leadership in unfamiliar contexts. When she arrived in Niger as the first woman to serve as Chief of Office Security Cooperation, managing a $240 million portfolio, she faced what many of us fear: being underestimated because of who we are.

“I was really worried that my gender was going to be my vulnerability. I thought it was going to be something that prohibited me from entering rooms that my predecessor had automatic open doors to.”

Instead of trying to prove herself through force or directness, Maia led with curiosity:

“I would sit down with them. I’m like, please tell me, what is your vision for your defense force? What do you think your capability gaps are? What do you think your strengths are? How can we as partners help you get there?”

The result? What she thought would be her weakness became her superpower. By listening first, she gained access to both the male military leadership and the women within the defense force, perspectives her predecessors couldn’t reach.

Your Takeaway:
When you step into a new role or environment where you feel like an outsider, resist the urge to immediately prove yourself. Instead, ask questions. Listen deeply. The trust you build through genuine curiosity will open more doors than credentials alone ever could.

SAVE THE DATE: Monday, December 22nd at 10am ET for a live conversation with Aamina Awan-Khan on “The Intersection of Identity and Purpose.” Aamina was the former Chief Partnerships Officer in the U.S. Department of State’s Bureau of Public Diplomacy and has held management roles with the Clinton Foundation, the United Nations and Credit Suisse AG. (Link to join)

The Identity Shift No One Talks About

One of the most vulnerable moments in our conversation came when Maia talked about switching from the Marine Corps to the Army after 10 years of service:

“I was really worried that when I took that name tag off that I wouldn’t know who I was. I had spent my entire career being a Marine officer, training to be one, hitting the highest standards to be as best as I could. And I loved being a Marine.”

This resonated deeply with me. I’ve witnessed so many leaders struggle with similar identity shifts: leaving a prestigious company, transitioning from corporate to nonprofit, stepping away from a title they’ve worked decades to earn.

But here’s what Maia discovered: “When I put on that Army uniform, I was like, oh, I’m exactly the same. Like actually nothing has changed about me.”

The uniform changed. The organization changed. The culture changed. But her mission, to serve her country, create opportunities for others, and lead with integrity, remained constant.

Your Takeaway:
Your identity isn’t your title or your organization. It’s the mission you’re committed to and the values you bring to every arena. When you’re clear on those, you can step into new contexts without losing yourself.

Communication Isn’t One-Size-Fits-All

Throughout her career, Maia has had to radically adapt how she communicates: from briefing generals in combat zones to negotiating with foreign military leaders in French to now working with nonprofit leaders in New York City.

She shared a funny example from her current role: “I will teach them a military term a week… I’ll walk in and say, OK, what’s the closest alligator to the boat? And they [respond with confusion in their eyes], what are you talking about?”

This isn’t just about learning new jargon. It’s about recognizing that effective leadership requires meeting people where they are, speaking in language that resonates with them, and being humble enough to ask when you don’t understand. And it means being willing to share the context of your language, too — that’s how you create authentic connection.

Your Takeaway:
As you move between contexts, whether that’s different departments, industries, or cultures, pay attention to how people communicate. What metaphors do they use? What matters to them? Your ability to translate your experience into their language will determine whether your expertise lands or falls flat.

The Myth of Being “100% Ready”

Near the end of our conversation, I asked Maia what she’d say to someone considering a big career leap. Her response was immediate:

“I feel, especially as women, we feel that we can’t take on a new opportunity or do something new unless we’re 100% prepared and ready to go. And I would say that a lot of these jumps that I took in these different arenas, I was not 100% ready to go, right? But I knew that once I got in there, I could learn.”

This is the permission slip so many of us need. We wait for certainty that will never come. We wait to feel completely qualified. We wait until the fear disappears.

Maia’s advice? “Comfort is the enemy of growth.”

She reminds her son daily:

“You have survived 100 percent of your hardest days.”

If you’re like me, you needed to hear this. I’m keeping this one on my “revisit weekly” list.

Your Takeaway:
Stop waiting to feel ready. If the opportunity aligns with your mission and values, if you’re willing to learn and have a support network to lean on, take the leap. The growth happens in the arena, not on the sidelines.

Building Trust Takes Time (and That’s Okay)

One insight that particularly struck me was Maia’s patience in building trust, whether with her diverse team in Niger or with military partners who weren’t used to working with a woman in her role.

“Trust, confidence and respect. It takes a lot of time to build that. And it comes with results. You have to prove yourself always.”

In our efficiency-obsessed culture, this can feel frustrating. We want to be direct, get to the point, make things happen fast. But Maia’s experience shows that sometimes the “efficient” path actually takes longer if people aren’t ready to trust you yet.

Your Takeaway:
When you step into a new leadership role, especially one where you’re breaking new ground, build trust before pushing for change. Show up consistently. Deliver on what you promise. Listen before you advocate. The relationships you build will determine what you can accomplish.

Translating Your Skills Across Arenas

Maia’s transition from military service to nonprofit leadership required more than just finding a new job. It required translating 20 years of experience into language and context that made sense in a completely different world.

“For veterans that are transitioning out of uniform, it’s really important to be able to translate your skills. We’re really good at listing off our technical capabilities... But that doesn’t work really well when I’m in a room full of nonprofit leaders.”

This applies to all of us navigating career transitions. Your skills are transferable, but you need to reframe them for your new audience.

Your Takeaway:
When making a career transition, don’t just list what you’ve done. Articulate what you’ve learned, how you think, what problems you solve, and how that applies to the new context. Your past experience is valuable. But only if you can help others see its relevance to their world.

Finding Your Mission, Not Just Your Next Job

What made Maia’s conversation so powerful wasn’t the impressive resume or the list of “firsts” she’s achieved. It was her clarity about her mission: creating pathways for others, serving with integrity, and being the best leader she can be while staying true to her values.

That mission has remained constant whether she was:

• The first woman to compete in the Naval Academy’s brigade boxing championship

• Managing a $240 million security cooperation portfolio in Niger

• Teaching at West Point

• Investing in women and girls as changemakers in New York City

• Building a speaking and storytelling portfolio

The arenas changed. The mission didn’t.

Your Takeaway:
Before you make your next career move, get clear on your mission. What are you ultimately trying to accomplish? What impact do you want to have? When you’re anchored to that, you can evaluate opportunities not by title or prestige, but by alignment with what matters most to you.

Your Next Move

If you’re considering a career transition, feeling stuck in your current role, or wondering whether you have what it takes to step into a bigger arena, I want you to sit with this question:

What is your mission? Does it need to change or do you need to change the arena?

Before you worry about your job title, your industry, your specific role, clarify your purpose. It will be your guide as you figure out what needs to change and be your an anchor when everything else shifts.

For Maia, it was creating pathways for others and leading with integrity.
What is it for you?

And once you know that? As Maia says: “Be bold. You just never know what is going to happen unless you take that leap and you jump into it.”

You’ve survived 100% of your hardest days. You’re ready for the next arena.

If you felt inspired by her story and want to stay in touch, connect with Maia on LinkedIn or visit her at voiceinthearena.com

What resonated most with you from this conversation? Hit reply and let me know. I read every response.

Leave a comment

Conversation Topics & Timestamps

Introduction & Background (00:00:00 - 00:05:10)

• Maia’s journey from boxing to military service to nonprofit leadership

• Growing up with a single mother in Buffalo, NY

• The value of hard work and education instilled early

The Naval Academy Journey (00:05:10 - 00:09:00)

• Being recruited for sports but initially rejected from the Naval Academy

• Using rejection as fuel: attending foundation school and reapplying

• Learning that persistence paired with strategic preparation opens doors

Boxing & Breaking Barriers (00:09:00 - 00:11:45)

• Why boxing after 9/11: building physical and mental resilience

• Becoming the first woman to compete in the brigade boxing championship

• Petitioning for change and creating pathways for women who follow

First Combat Deployment (00:11:45 - 00:14:30)

• Leading Marines in Iraq at age 22-23 for 15 months

• Focusing on the team’s preparation rather than personal fear

• Learning to put people first as a leadership principle

Becoming a Commanding General’s Briefer (00:14:30 - 00:19:12)

• The power of being a good communicator and knowing your audience

• Transitioning to aide-de-camp: shadowing C-suite level decision-making

• How mentorship and sponsorship opened doors to become a Foreign Area Officer

Becoming a Military Diplomat (00:19:12 - 00:24:00)

• Three years of training: master’s degree, learning French and Kiswahili

• Traveling to 25 African countries to understand the landscape

• How early opportunities create ripple effects throughout your career

Switching from Marines to Army (00:24:00 - 00:30:05)

• The identity crisis of taking off the Marine Corps name tag

• Realizing the mission stays the same regardless of the uniform

• Balancing professional goals with personal life and family

Leading in Niger (00:30:05 - 00:41:00)

• Managing a $240 million security cooperation portfolio

• Turning perceived vulnerability (being a woman) into a superpower

• Leading with listening: understanding your partners’ vision first

• Pioneering the first Women, Peace, and Security program

• Building trust through results and authentic partnership

Communication & Cultural Intelligence (00:41:00 - 00:45:00)

• Adapting communication style across diverse teams

• Leading with emotional intelligence and empathy, not just directness

• The importance of timing in negotiations and relationship building

Transition to Education (00:45:00 - 00:46:30)

• Teaching at West Point as a highlight of military career

• Mentoring the next generation with the knowledge she wished she’d had

Retiring & Joining Nonprofit World (00:46:30 - 00:52:00)

• Choosing purpose over profit after retirement

• Finding Amplify Her Foundation: investing in women and girls in NYC

• Translating military skills to nonprofit language

• Learning to be humble and curious in a new arena

The Power of Storytelling (00:52:00 - 00:55:00)

• Why storytelling matters: combating bias and creating connection

• Representing female veterans and changing perceptions

• Finding joy in unexpected places through shared stories

Advice for Taking the Leap (00:55:00 - 00:57:23)

• You don’t need to be 100% ready to make a move

• Comfort is the enemy of growth

• “You have survived 100 percent of your hardest days”

• The importance of doing something scary and trusting yourself

If you found this post valuable, consider clicking to leave a ❤️ so more people can discover it on Substack.

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May you lead without limits,

What started as a discussion about navigating AI and remote work became something much deeper: a masterclass in human-centered leadership during times of massive transformation.

Dan’s story isn’t your typical Silicon Valley narrative.

It’s one of immigrant resilience, calculated risk-taking, and the kind of thoughtful leadership that prioritizes people alongside profits.

In just 14 months, he helped transform Collectors from an $850 million acquisition into a $4.3 billion valuation; not through aggressive layoffs or flashy technology plays, but through sustainable growth and genuine investment in people.

Here’s what I learned from our conversation, and what you can apply to your own leadership journey.

Tip: Scroll to the bottom for a timestamped outline of our conversation so you can jump to the parts you care about most.

Everything Is Made Up. So Why Not Make It Better?

One of the most liberating things Dan shared was his perspective on change:

“Everything that you have that’s around you, that you do, that you’re living in, was made up by someone or a group of someones. There really is no reason why you couldn’t be and may not be one of those someones to build it for the next generation.”

This mindset comes directly from his parents’ story. As Vietnamese refugees who survived unimaginable hardship: cargo ships, refugee camps, and starting over in a completely foreign country with nothing. They taught him that no professional challenge could ever be as difficult as what they overcame.

But here’s the key: Dan doesn’t let this perspective make him reckless. Instead, it removes the paralyzing fear of the unknown while maintaining respect for the complexity of the work ahead.

Your Takeaway: When facing a daunting change or challenge, ask yourself: “What’s actually at risk here?” Often, our fears are disproportionate to the reality. This doesn’t mean being careless. It means being courageously strategic.

Real M&A Wisdom: Respect What Came Before

When Dan joined Collectors, he found a 35-year-old company with 750 employees and just 22 people in tech. The company was “collapsing under their own success:” outdated technology, manual processes, Post-it notes instead of digital systems.

The easy move would have been to sweep clean and start fresh.
He didn’t do that.

Instead, Dan spent time with each person on the team, understanding their strengths, their institutional knowledge, and their potential. He found people who had been with the company for 25-30 years, an almost unheard-of tenure in tech.

“You never hear about companies that have people stay for that long,” he told me. “That’s a wealth of information and stories and knowledge that you want to tap into if possible.”

His approach was to build career ladders, create clear departments, hire managers who understood enterprise-scale systems, and give people room to grow into specialists rather than remain overwhelmed generalists.

Surprisingly, he retained the majority of the original team through this transformation. Not because he had to, or from fear, but because it aligned with his values and was the smart thing to do.

Your Takeaway: Whether you’re joining a new company or leading a transformation, your first job is to understand what already works and why. The people who’ve been there have context you’ll never have. Your job is to create the structure and tools that give them the chance to thrive. The goal shouldn’t be to retain the team at all costs, but it’s a huge mistake to dismiss without first trying to build with them.

Make Trade-Offs Transparent (But Know Your Audience)

Here’s something Dan admitted publicly for the first time during our conversation: the board was questioning his abilities during that first year.

Revenue wasn’t improving fast enough. He was “exploding the budget” by hiring new people. The backlog was actually getting worse because he was adding process and onboarding people, which took existing team members away from their work.

They were seriously considering replacing him.

What saved him? Clear communication about trade-offs, calibrated to each audience.

For the board, Dan kept explanations high-level: here are the metrics improving, here are the signals to watch for, here’s why sustainable growth matters more than quick fixes.

When they asked about his strangler fig tree pattern for managing tech debt (gradually replacing old systems by building on top of them), he could see their eyes glazing over within 30 seconds. He adjusted: “Just trust me.”

For his team, the opposite was true. Dan practices radical transparency: “I tell them 100% of what I’m going to do, what the plan is.” He wants everyone, from engineers to marketing to HR, to understand the company’s revenue, the reasoning behind decisions, and the trade-offs being made.

This transparency meant his team understood why they were keeping ancient infrastructure in a closet (fire risk, night & weekend work, and more) while investing resources elsewhere. They knew why they couldn’t automate everything immediately. They understood the North Star and could make good decisions without constant oversight.

Your Takeaway: Different stakeholders need different levels of detail. Your board needs confidence in the direction and evidence of progress. Your team needs context to make good daily decisions. Neither is more important. They’re different jobs requiring different information.

The Real Cost of Moving Too Fast

While other companies were doubling and tripling their engineering teams in 2021-2022, (highlighted by Amazon raising their salary cap from $250K to $360K and everyone doing a land grab for talent), Dan grew his team by just 5-10 engineers.

The board questioned this too: “These companies are pulling in thousands, tens of thousands of engineers. You only increased by five or ten engineers. Why is that? Are you incompetent?”

His response?

“I would put a bet that they will all have to course correct how much they’re spending on engineers in the next couple of years... They’re paying high amounts now, but the ROI they’re getting from each engineer won’t match that.”

And yet behind his confident answers, Dan didn’t know for sure. He was trusting his instincts and his common sense. What other companies were doing didn’t make sense. His critical thinking paid off.

He was right. Those companies are now doing 10% layoffs, cutting salaries, and removing benefits. Meanwhile, Collectors continues to grow sustainably, adding salaries and benefits even in today’s economy.

Your Takeaway: Resist the pressure to follow what everyone else is doing just because “that’s what successful companies do.” Sustainable growth (in headcount, in technology adoption, in any transformation) almost always beats rapid scaling. The fast way is often the slow way in disguise.

AI Is a How, Not a What

When I asked Dan about implementing AI, his response was refreshingly pragmatic. He started building an AI department in 2021-2022 with one person whose job was simply to “tinker, experiment, and try a lot of different things.”

Four years later, they released an AI feature in their mobile app that can scan any trading card and identify it within seconds. But it took four years of experimentation to get there.

Meanwhile, his team experiments with 15-30 different AI startups and platforms at any given time. Everything from code generation to automated performance reviews to financial forecasting.

His philosophy?

“AI in general, to me, the way that you should think about it is it’s a how, not the what. It’s not the final goal.”

Some experiments work brilliantly. Dan now uses AI to draft performance reviews that sound exactly like him and are actually less biased than his own first drafts because they don’t suffer from recency bias.

Other experiments fail spectacularly. Ask an AI tool “how much revenue did we have last quarter?” twice, and get two different answers? That’s not ready for production.

The key is that Dan’s team is always experimenting, always learning, always asking: “What problems do we need solved?” first, then exploring whether AI can solve them better than manual processes.

Your takeaway: Don’t adopt AI because you feel you should. Identify the problems you need to solve. Problems that exist whether AI exists or not. Then explore whether AI solves them faster, better, or cheaper. And expect that half your experiments will fail. That’s not a bug; it’s the feature of experimentation.

Fighting for What You Believe In

Near the end of our conversation, I asked Dan what gets him “bent out of shape” at work. His answer was telling:

“The thing that really affects me the most at work is when we aren’t trying to push ourselves to be better.”

He shared an example from last year when the company was considering an expensive acquisition to enter a new business line. Dan believed they could build it themselves, better and faster. His product counterpart disagreed: they didn’t have the time, resources, or priority.

Dan made a bet:

“Give me a month. If you can hold off on that deal for a month, I think I can show enough progress to convince you otherwise.”

He got his month. He gave two engineers a project, a small budget, and a bounty for completion. Within three weeks, they had a working proof of concept. The acquisition was declined. The product they built became hugely successful, generating millions in revenue.

Your Takeaway: Sometimes leadership means putting your conviction on the line. Not recklessly, but strategically. When you deeply believe something is possible, and you’re willing to do the work to prove it, ask for the space to try. The worst case? You learn something valuable. The best case? You create something transformative.

The Why Behind It All

What struck me most about Dan wasn’t his technical acumen or his business results, impressive as they are. It was his clarity about why he does what he does.

He kept coming back to his parents, to the families who sponsored them, to the opportunities he was given.

“I just don’t want to waste it. I want to make sure that I’m making the most of it.”

But his why extends beyond gratitude. He has a vision of what’s possible when we help each other:

“Imagine a world where we’re all helping each other get the maximum... helping everyone to actually be the best version of themselves, how much more fulfilling life could be for each one of us, but also how much better the world could be for all of us.”

This isn’t just feel-good philosophy. It’s the foundation of every decision Dan makes: Will this help people be the best version of themselves? Will this make the world better?

When your why is that clear, the how becomes easier to figure out.

What This Means for Your Leadership

Here’s what I’m taking away from my conversation with Dan, and what I hope you’ll consider for your own leadership:

1. Reduce fear with perspective. What you’re facing likely isn’t as hard as your mind makes it. Ground yourself in what’s actually at risk.

2. Invest in the people who are already there. Transformation doesn’t require replacement. It requires structure, clarity, and space to grow.

3. Make trade-offs explicit and appropriate. Your board doesn’t need implementation details. Your team doesn’t need to be shielded from hard truths. Give each the right level of transparency so they can do their part.

4. Resist the pressure to move at everyone else’s pace. Sustainable growth beats rapid scaling nearly every time.

5. Experiment relentlessly with new tools and technologies. But always start with the problem you’re solving, not the shiny new solution.

6. Put your conviction on the line. Use your own judgment and critical thinking. When you believe something deeply, be courageous and ask for the space to prove it.

7. Know your why. It’s what will sustain you when the board is questioning you, when the transformation is messy, when the easy path looks tempting.

Dan’s journey from a kid coding games on a TI-82 calculator to a CTO who’s helped build a multi-billion dollar company isn’t just a success story. It’s a blueprint for human-centered leadership in an era of constant change.

The technology will keep evolving. The business models will keep shifting. But the fundamental work of leadership, helping people become the best version of themselves while driving toward a meaningful vision, that remains constant.

Want to connect with Dan? Find him on LinkedIn or visit his website at danvantran.com. And if you’re curious about the world of collectibles and how technology is supporting this thriving community, check out collectors.com to see the innovative work his team is doing.

What resonated most with you from this conversation? Hit reply and let me know. I read every response.

Conversation Topics & Timestamps

Jump to the topics that interest you most:

• 00:00 - 02:23 - Introduction and Dan’s background overview

• 02:23 - 04:24 - Why Dan is speaking more and navigating the “weird time” for tech leaders

• 04:27 - 08:50 - Dan’s family immigration story and his father’s journey into tech/telecommunications

• 08:50 - 12:50 - How Dan taught himself to code on a TI-82 calculator (and convinced his parents to let him keep it)

• 12:50 - 15:45 - Getting into trading card collecting and the connection to his sponsor families

• 15:45 - 19:30 - How Dan discovered Collectors.com and decided to join as CTO

• 19:30 - 24:30 - The state of Collectors at acquisition: 750 people, 22 in tech, systems “on fire”

• 24:30 - 27:45 - The approach to transformation: respecting existing talent vs. wholesale replacement

• 27:45 - 34:20 - How to navigate change you’ve never done before: removing fear, defining “good,” and finding the right experts

• 34:20 - 37:40 - The importance of getting that first milestone right in change management

• 37:40 - 44:15 - The board’s concerns during the first year: spending more, moving slower, and nearly being replaced

• 44:15 - 49:00 - Making strategic trade-offs: keeping infrastructure in a closet, manual on-call, short-term vs. long-term investments

• 49:00 - 52:15 - Different levels of transparency: what the board needs vs. what your team needs

• 52:15 - 56:45 - Why Dan only grew by 5-10 engineers while others hired thousands (and why he was right)

• 56:45 - 1:02:40 - The AI journey: starting with one person in 2021, building to 10-15 engineers, launching card scanning feature after 4 years

• 1:02:40 - 1:05:30 - Corporate AI experiments: testing 15-30 tools at once, what works (performance reviews) vs. what doesn’t (financial data)

• 1:05:30 - 1:09:15 - AI as a “how not a what”: always start with the problem, not the technology

• 1:09:15 - 1:12:30 - What gets Dan bent out of shape: when we stop pushing ourselves to be better

• 1:12:30 - 1:13:45 - The acquisition bet: convincing leadership to give him one month to build instead of buying

• 1:13:45 - 1:17:17 - Dan’s “why”: honoring those who helped him and helping others be the best version of themselves

Want more from me?

Substack LIVE Conversations

SAVE THE DATE: Monday, December 22nd at 10am ET for a live conversation with Aamina Awan-Khan about “The Intersection of Identity and Purpose.” Aamina was the former Chief Partnerships Officer in the U.S. Department of State’s Bureau of Public Diplomacy and has held management roles with the Clinton Foundation, the United Nations and Credit Suisse AG. Link to come next week.

If you missed my conversation yesterday with military veteran and philanthropy leader, Maia Molina-Schaefer ( on Substack), stay tuned. I’ll be publishing our full conversation and a written digest next week.

Catch up on all of my Substack Lives here.

Work with me in 2026

And there is still one spot left for 1:1 coaching with me in Q1 2026. I’ve also just recently opened up a limited set of corporate group coaching and facilitation workshops. If you’re interested in either, book a 15 min free strategy call.

May you lead without limits,

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