Each post contains the full recording of our conversation, my reflections, and a timestamped summary of the entire conversation at the very bottom of the post. Many thanks to my guest !

I’ll be honest — I walked into this conversation with a small amount of unconscious bias.

When I hear “retired Major General,” my movie-brain goes straight to the caricature. Rigid. Top-down. Command and control. The kind of leader who barks orders and expects silence in return. That’s the story Hollywood has been selling for decades, and most of us have absorbed it without questioning it much.

96% of American adults have never served in the military. So we fill the gap with Patton. With the archetype of the general who was a “true badass” — Robert’s words — for a particular moment in time, but whose methods would crater any modern organization.

Then I spent 40 minutes talking to Robert Mixon, Jr.

Within the first few minutes, he said something that stopped me: “I think I’ve made 99.5% of all the leadership mistakes you can make.”

He said it matter-of-factly. No performance, no setup. Just the plain truth from a man who commanded a division of thousands of soldiers, ran a manufacturing company as president, led a nonprofit, and has been coaching leaders for over a decade. He wasn’t building to a lesson. He was just telling you who he is.

That’s when I understood. Robert doesn’t represent the caricature of military leadership. He dismantles it — not by arguing against it, but simply by how he shows up.

All anybody has to do is spend two minutes with him, and they can feel it.

Chaos isn’t the exception. It’s the condition.

Robert’s framework for all-in adaptive leadership starts with an honest diagnosis of where we are right now.

He defines chaos as “raging uncertainty — where we don’t know what we don’t know.”

That phrase stuck with me. Because most of us have a vague sense that things feel hard right now. Economically. Organizationally. In ways that are hard to name.

Raging uncertainty is the language. It’s not a temporary disruption we’re waiting to resolve. It’s the water we’re swimming in.

And here’s the thing Robert and I landed on that I talk about all the time: we are all, on some level, preschoolers on the inside.

We want to know what’s for dinner. What time we’re supposed to be on the call. What the schedule looks like.

Kids respond well to preschool precisely because there’s structure — circle time, then weather, then recess, then snacks.

As adults, we’ve layered sophistication over the same basic need. We want certainty. And when it disappears, we struggle.

I recognize this in myself. When I’m anxious, I start talking faster. I fill the airspace. And all I’m doing, as a leader, is making everyone around me more anxious, too.

The leader’s job isn’t to pretend certainty exists. It’s to create enough of a container — a direction, a shared sense of purpose, a set of values that hold — so that people can function without it.

That’s what Robert calls setting the azimuth.

The Big Six — and what each one actually means in practice

Robert has distilled his leadership thinking into what he calls the Big Six principles of all-in adaptive leadership. He’s clear that these aren’t original to him. He learned them from watching great leaders, studying under people like General Colin Powell, and getting them wrong himself before he got them right.

I want to give each one the space it deserves — because these are not just principles to agree with. They’re practices to build.

1. Set the azimuth.

An azimuth is a military term for a direction of travel — a compass bearing that keeps you oriented even when the terrain changes. Robert uses it to mean your organizational true north: mission, intent, values, and the specific behaviors that bring those values to life.

Here’s what makes this different from the version most organizations do: it has to be built with the team, not handed down to them.

Robert walked us through what this looks like in practice. You sit down together and ask: Who are we? What do we do? Why do we do it? You work through mission and intent and values collectively. You define what your values actually mean in behavior — because if you don’t define them, people make up their own definitions, and those definitions are usually not right.

The azimuth also has to be measurable — which is where I think this approach really stands out and can have a lasting impact.

Robert reminded us all: “that which is measured gets done.” He learned this as a cavalry officer and as a manufacturing president.

Vague aspirations don’t hold. But when you can show progress, people see the mission isn’t just words.

And then you sustain it. Not announce it and forget about it. You persist and make it last.

2. Listen.

Robert’s mom told him: God gave you two ears and one mouth for a reason. His mom is 93. He says he still hasn’t fully delivered on her advice, but he’s working on it.

Stephen Covey said: “Listen with the intent to understand, not to reply.” Robert’s honest that 99% of us do the latter.

But there is a better way.

The practical tool he uses — and teaches — is the two-second rule. Before you respond to anyone speaking to you, wait two seconds. Just two.

The reasons are better than you’d expect.

First: the person may not be done. Interrupting is a signal of disrespect, whether you intend it or not.

Second: you give yourself time to actually think before you speak, instead of just blurting.

Third: and this one is the most powerful — when you give people a chance to finish and then wait before responding, they feel regarded. They feel like what they said mattered. That feeling, built over time, creates trust.

Robert says if you practice the two-second rule consistently for 21 days and audit yourself on it daily, you’ll watch people’s behavior change. Not because you gave them feedback. Because yours changed.

I added two more reasons:

One: if you’re having an emotional reaction to what someone said, the pause gives you a chance to catch it before it lands on the other person.

And two: when we rush, we signal anxiety. People feel that energy and mirror it back. The pause is not just a listening tool. It’s a regulation tool.

3. Trust and develop your people.

You cannot scale what you won’t release. Leaders who hoard decisions create teams that wait to be told what to do — and in a world of raging uncertainty, that is a dangerous dynamic.

Robert frames this simply: you have to trust people if you want them to grow. And developing them is not optional. It is the work.

4. Do the right thing when no one is looking.

Before anyone else. Make sure you are leading by example.

This is where Robert starts when he works with leaders who feel overwhelmed. Not with the frameworks. With the personal mission statement.

Two or three sentences: Who am I? What do I do? Why do I do it? Write it. Write the values and operating principles that follow from it. What can people expect from me? What do I expect from them? Sign it. Date it. Share it with your team.

Now you have put a marker in the ground that you can be held to — and that you can hold yourself to. Robert calls these “daily audits.” Are you walking the talk? Not sometimes. Habitually. Not episodically.

What I find so powerful about this is that it mirrors what I work on with my clients in the ME Work — the inner operating system that makes everything else possible. When you haven’t taken care of yourself, you are not able to focus on the people around. you.

Robert arrived at the same place through the military, through boardrooms, through coaching: The first person you have to lead is you.

5. When in charge, take charge.

This is the one that sounds like the caricature — but turns out to be its opposite.

When Robert says “take charge,” he does not mean be loud, rigid, or directive. He means: be the calm.

Embody what he calls tactical patience. Be the one who says, “We may not know all the answers, but we have an azimuth, we have each other, and we are going to get through this together.”

And then — critically — underwrite mistakes. Not punish them. Learn from them. That distinction is the difference between a team that takes initiative and a team that pretends to.

6. Balance the personal and professional.

Most people hear “balance” and think: how many hours am I on Zoom? Am I the last one to leave the office?

Robert reframes it entirely. You cannot manage time — it is finite. What you can do is take more ownership of how you show up within it. The way you do that is by sustaining your four levels of energy: physical, mental, emotional, and spiritual.

Think of them as battery levels. If they’re depleted, you’re running the five previous principles on fumes. If they’re protected and restored, you have something real to give.

This isn’t soft. It’s structural. A depleted leader creates a depleted team.

The two questions that define your culture

One of the most clarifying moments in the conversation came when Robert posed a simple scenario.

Something goes wrong in your organization. It happens daily — that’s the world we’re in. The boss turns to someone on the team and asks a question.

Option one: “What were you thinking?”

Option two: “What did we learn here?”

Feel the difference. Not just in tone. In what each question creates.

The first is a verdict dressed up as a question. It signals blame. It tells your team that mistakes are dangerous. And in a world of raging uncertainty, if your team believes mistakes are dangerous, they will stop making decisions. They will wait. They will cover themselves.

The second is an invitation. It signals learning. It tells your team that their judgment is trusted, even when it falls short. It builds what Robert calls a culture of commitment — where people are genuinely all in because they belong, they matter, and their stumbles are treated as part of the work.

Robert calls this the difference between “sins of commission” and “sins of omission.”

Mistakes made while genuinely trying to do the right thing within the mission and values are supposed to happen. They are not a crisis. They are the necessary data and the signals you need to lead well.

Toxicity lives in the blame game, he said. Not sure if you believe him? Just look around you. In the organizations with the greatest distrust, the greatest fear — fear of blame is likely one of the core reasons.

Respect is specific, not aspirational

Here’s where the conversation got practical in a way that surprised me.

We started talking about how you actually bring values to life — not just post them on a wall and call it culture. Robert pushed on the word “respect.” Most organizations say they value it. But what does it look like?

He walked us through a workshop where a team sat with that question in silence. Then the ideas starting coming out. They weren’t bad, but none of them were measurable — all of them were subjective and required context to assess.

Robert went back to “that which is measured gets done,” and he challenged the team, “What if we just do things on time?”

The room shifted.

That’s a behavior that isn’t up for interpretation. It’s measurable. And every person on that team had felt the disrespect of the opposite — meetings that ran long with no agenda, colleagues who arrived late without acknowledgment, time treated as an abundant resource when it is the one thing no one can get back.

Robert told us he estimates he’s lost roughly 8,000 hours of his life in meetings with no agenda, no clear start, no clear end. Just stories about trout fishing and nothing that had anything to do with why people were in the room.

Being on time is not a small act of professionalism. It’s a statement. It says: I value your time. I follow through on commitments. I show up the way I said I would.

The question he left us with: what behavior in your organization, if your team committed to it and sustained it for 21 days, would actually shift the culture?

That’s not rhetorical. It’s where to start.

Managing up when the culture isn’t there yet

Not everyone listening leads from the top. And not everyone at the top is creating the conditions Robert describes.

So I asked him directly: what do you do when you see the need but you’re not the one setting the tone for the whole organization?

His answer was one of my favorites in the entire conversation.

Don’t walk into your boss’s office and tell her she’s doing it wrong. Even if she is. Especially if she is. You will raise her defenses, and you will lose before you’ve started.

Instead, ask for a pilot. In your own team. For 90 days. Give your boss regular updates — what Robert calls a “back brief” — showing what you’re learning and what value it’s creating. Let her see results without feeling threatened by critique.

Evidence is more powerful than argument. Always.

If you can create a pocket of culture within your own sphere of influence, people notice. They want what you have. The culture spreads not because someone mandated it, but because someone made it visible, and real and worth wanting.

What I took away

I asked Robert at the end what he wanted people to walk away with.

He said: “Leading effectively through chaos is hard work. It’s adult work. But it’s doable if you’re committed to the journey.”

No promise that it gets easy. No guarantee that the frameworks fix everything. Just the honest invitation to commit to the work — of leading yourself, and then of leading others — with intention and consistency.

I left this conversation thinking about my own preschooler tendencies. The moments when raging uncertainty has made me want certainty so badly that I’ve defaulted to control, to speed, to telling instead of asking. The moments I’ve broken the two-second rule. The times I’ve asked “What were you thinking?” instead of “What did we learn here?”

I also left thinking about what it means to carry 33 years of service and still introduce yourself by saying: I’ve made almost every mistake there is. That posture — that refusal to perform authority — is exactly what I mean when I write about leading from the inside out. It’s the ME Work made visible. It’s what genuine credibility looks like.

Robert didn’t just talk about a different kind of leadership. He was a living example of it for 40 minutes.

All anybody has to do is spend two minutes with him, and they can feel it.

If you can spare the time, watch the video. You won’t regret it. Before the Substack Live, I was feeling tired (a terrible night sleep) and behind on my day. But in our 15 min right before the Live started, talking with Robert, I just felt myself light up.

That’s what real leadership looks like. It isn’t about the title, or the authority. It’s about being able to see someone fully and to help them see themselves just as completely. It is a gift. And conversations with gifted leaders like Robert remind me of the importance of simple actions done with great strategic intent and care.

That’s the “all in leadership” that Robert teaches, and it’s exactly what the world needs more of right now.

About Robert Mixon Jr.

Robert is a retired U.S. Army Major General, former corporate executive, and founder of Level 5 Associates. He is the author of We’re All In and The Power of Being All In, both of which include tools you can start using today. The first chapter of each book is available as a free download at level5associates.com.

He writes All In Adaptive Leadership Insights on Substack, where he publishes practical leadership tools multiple times each week. Go find him.

If you enjoyed this post, consider giving it ❤️ to help more people find it on Substack. And consider sharing it with a leader you know who is navigating tough times — this might be exactly what they needed to help them lead calmly through the chaos of our times.

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May you lead without limits,

Your Timestamped Guide to the Conversation

Timestamp — What We Covered

00:00 — Welcome and introductions — Robert’s background across military, corporate, and nonprofit leadership

03:28 — Robert’s origin story: “I’ve made 99.5% of all the leadership mistakes you can make”

05:01 — Defining chaos as raging uncertainty — and why humans crave certainty at every age

07:23 — Introduction to All-In Adaptive Leadership and the Big Six principles

07:38 — Principle 1: Set the azimuth — true north, mission, values, behaviors defined collectively

07:53 — Principle 2: Listen — the two-ear, one-mouth rule and the gap between what we know and what we practice

08:50 — Principles 3–6 overview: trust and develop, lead yourself first, when in charge take charge, balance personal and professional

09:41 — Reframing “work-life balance” as energy management across four levels

11:01 — Where to start when the Big Six feel overwhelming — begin with a personal mission statement1

2:07 — Vulnerability as a leadership strength, not a weakness

14:02 — Learning the Big Six from General Colin Powell

14:51 — The two-second rule for listening — and why it changes team behavior within 21 days

16:06 — Kathy adds: the two-second rule as an emotional regulation tool, not just a listening tool

17:10 — “Fire, ready, aim” — why speed without pause is a bad technique in leadership and in life

18:00 — What it looks and feels like to be the calm in the chaos

20:28 — The fix-it trap: when problem-solving becomes the wrong default

21:36 — The fairy tale of the all-knowing leader and why directive leadership is largely ineffective

22:52 — Building buy-in through collective problem definition — getting people part of the solution

23:21 — Belonging as a fundamental human need and what it takes to create it at work

24:03 — Sins of commission vs. sins of omission — underwriting mistakes vs. the blame game

24:34 — The two questions that define your culture: “What were you thinking?” vs. “What did we learn here?”

25:31 — The five levels of culture and why levels one and two leave people feeling like they don’t belong

27:44 — Respect as a leadership value — and what behaviors actually bring it to life

29:57 — The 8,000 wasted hours and why meeting discipline is an act of respect

31:20 — How the two-second rule and meeting discipline together can shift an organizational culture

32:02 — Building accountability through shared, written, signed commitments

34:00 — The azimuth-setting process in practice — how to build it collectively with your team

34:16 — Managing up when the culture isn’t there yet — the 90-day pilot program approach

36:43 — “Evidence is more powerful than critique”

37:27 — Closing reflections: it’s adult work, it’s doable, it requires commitment to the journey

38:53 — Kathy’s reflection: busting the military leadership caricature

39:24 — Robert’s response: the misidentification of military leadership and what it actually looks like

A while back, I wrote a piece about the uncomfortable topics you should share with your direct reports during onboarding.

It’s unusual to dive into fears, risks, and disappointments at the outset. But those honeymoon, sunshine-filled days are exactly when you both should talk about the prospect of dark times.

Beyond the topics themselves, what I was really getting at is that while a relationship is still forming and still positive, that’s the best time to talk about the tough topics that will only get more awkward and difficult over time.

When the inevitable challenges arise, and they will, the fear that you and your direct report will be feeling will cloud your judgment. It’ll create suspicion and doubt. It will erode trust when you need it most.

What I didn’t share in that piece is how you can guide your people to more productive behaviors and how to work with you (a la your user manual).

In a world dominated by one-line tweets and abbreviated text messages, if I were leading a team today, I’d opt to write a letter to share my thoughts.

Here’s what I’d say. Please feel free to borrow.

A letter to my team

Dear team,

I’m writing to you because I want our working relationship to be as strong as possible, not just because it will help us achieve our mission and goals, but because I believe that one of the greatest gifts of work is the people you meet and the relationships you build.

Your talents and efforts will help us achieve our goals, but that’s small potatoes. I value you more than simply as a body in a seat.

What matters as much and perhaps more is how your energy, personality, and wisdom will enrich the experience of everyone on this team, including mine. You being here will make this journey more enjoyable and more memorable.

That said, I also recognize that we each have roles to fill, and that even if things are working well now, that may change in the future.

Whether it’s market dynamics, your interests, or my behaviors, the nature of work is that things change and not always positively.

Preparing for tough times can go a long way toward ensuring we do what’s best for the organization and preserve our relationship, which I hope lasts long beyond our time working together.

My mandate as a leader isn’t just to hit our short-term goals — annual targets and the like — it’s to create an organization that delivers on its promises, functions well, and has a long-term, sustainable future.

I hired you not just because you met the criteria in the job description, but because you possessed these critical attributes:

• A deep desire to grow and develop your skills and your career

• An alignment with the mission of our organization that goes beyond your functional role

• A belief that working together, we can accomplish more than if we were working apart

With all this in mind, I wanted to share with you what I wish my bosses had shared with me when we first started working together.

1. Your potential is infinite, but only if you manage it. If you see work in other areas you are interested in, ask about them. If there is a project you want to be assigned to, tell me. If you want to develop into a different role, say it. Help me help you.

2. Help me focus. My time is far more limited than my role demands. I care about you and your work, and I don’t think about either enough. I need you to make it easy for me to focus on what matters. Weekly, brief summaries of progress and obstacles, preparing for our 1:1s with a structured agenda, and creating dashboards that are easy for me to review are just some examples. Not sure, send a draft to me and let’s workshop it together.

3. Debate openly and often. Your thinking elevates the team's thinking. We will only arrive at the best answers if we can openly discuss and debate our ideas. Please know that even if I don’t agree with you, I value diverse insights, shared thoughtfully far more than I will ever value groupthink.

4. Know the why. Experimentation and exploration are valuable, but only if there is a hypothesis we are testing. If you aren’t sure about the why, ask until you get a clear answer. Always be willing to cut work that lacks a clear purpose.

5. Feedback is a gift. If something isn’t going well in our work together, tell me. Nothing will be gained by waiting. If it’s something I wasn’t aware of, give me a chance to own it. If it’s something I don’t agree with, you deserve to know. Feelings can fester, frustrate, and distract. Don’t let them.

6. When it’s time to go. Let’s talk it out and let’s plan it out. We don’t have to be dramatic, and we don’t have to have it hurt our working relationship. The best organizations have succession plans. Ideally, we’re planning together through the end and beyond.

My career was built on relationships: colleagues, bosses, clients, and partners. It is and was the way of the world. If you agree, then invite you to discuss any of the above points with me at any time.

Our journey together will not last forever. Let’s make the most of the experience and set ourselves up for far more than our shared tenure.

With respect and appreciation,

Not vaguely uncomfortable. Not mildly skeptical. Scared. The kind of scared where you watch everyone else jump in and you tell yourself you’re being thoughtful when really you’re just standing at the edge.

Here’s what made that strange: I am not someone who usually hangs back from technology.

I built some of the first websites on the internet. I walked the halls of Sand Hill Road, helping Silicon Valley’s most ambitious technology innovators bring their ideas to the financial markets. I was part of the team that helped launch one of the first video streaming platforms: Hulu. I remember when all of that felt like science fiction.

And yet. In 2023, when people I respect were already years deep into AI, I was still watching from the door.

I’ve been sitting with why that was. And a conversation I had with Kristi Pihl gave me language for something I think I already knew. (Watch the full conversation here).

Kristi is a Northwestern-trained mechanical engineer who has been building AI systems since 2017. Her work earned a TIME Best Invention in AI in 2019. She has spent two decades as a strategic tech advisor inside some of the most complex organizations in the world. She knows this technology from the inside.

And when we talked, she spent almost no time on the technology itself.

She kept coming back to this: AI is a mirror. It is a language-based model designed to reflect back what you give it. Which means if you approach it with fear, with defensiveness, with a need to look capable before you actually are... that is exactly what gets amplified.

She called it an accelerant. Not just an amplifier.

“If you’re already going to make the wrong turn,” she said, “you’re just going to make it faster.”

I’ve been thinking about that in the context of my own 2023 self. Because the fear I felt wasn’t really about the technology. It was about what the technology might reveal. About gaps I hadn’t named yet. About a version of my thinking that might not look as sharp under a microscope. About being exposed as a novice, undeserving of my title or my authority.

The fear was mine. AI just had the potential to show it to me faster.

Your C-suite is probably not afraid of AI.

They’ve done the work. They’ve committed budget, assembled a task force, chosen a platform. They have a plan and they are executing it.

But I want to ask you something.

When the board asked about your AI strategy, did you answer from clarity or from pressure? Did you build the plan because you knew what your organization needed, or because the alternative felt like falling behind? Was it a decision from your best thinking, or a decision from FOMO dressed up as strategy?

Kristi sees hundreds of organizations from her vantage point as an advisor and investor, and there’s a clear pattern: almost every organization she encounters right now believes they are behind. Behind their competitors. Behind the market. Behind some imaginary benchmark set by a press release from a tech CEO whose actual numbers, she noted, do not hold up to scrutiny.

The pressure is real. Boards are breathing down necks. Middle managers are automating workflows before anyone has asked whether those workflows were actually the problem. Everyone is running. And running faster, she reminded me, in the wrong direction is worse than running slowly in the right one.

Here’s the thing: neuroscience and psychology are aligned on this. Decisions made out of fear are rarely good ones. The bear chasing you in your mind doesn’t actually exist. The tiger is not in the room. What is in the room is a manufactured sense of urgency, a FOMO cycle fed by headlines, and a leadership team that has not yet had the harder conversation underneath the AI conversation.

The harder conversation is about what AI cannot fix.

It cannot fix a product that doesn’t fit its market. It cannot fix a pricing model that isn’t resonating. It cannot fix teams that have stopped communicating honestly with each other. It cannot fix a culture where people are overtaxed, understaffed, and quietly disengaged.

What AI will do is accelerate all of those things. Amplify them. Make them more visible, faster, at a greater scale.

This is where I keep coming back to the work I do with senior leaders. Not the AI strategy. The ME Work underneath it.

Because the leaders I coach who are quietly questioning their AI choices are rarely questioning the tools. They’re questioning whether their organizations are actually ready to use them well. And that question almost always leads somewhere more personal: do my teams trust each other enough to have the conversations that would tell us the truth? Are we making this decision from our best thinking, or from our fear of looking like we don’t have the answers?

Kristi described it this way: the leaders who use AI well already have the native judgment to evaluate it. They can tell when it’s being sycophantic. They can sense when it’s pulling from a random source instead of settled science. They have the critical thinking to know when to trust the output and when to push back.

That judgment takes time to build. It takes reps. And here’s the existential problem: if we automate the work that builds that judgment before the next generation has developed it, we don’t just lose the output. We lose the succession pipeline. We raise leaders who have offloaded their thinking before they ever owned it.

You can offload a task. You cannot offload understanding.

So what do you actually do with this?

There’s no skipping the hard part. Because the hard part is the point.

The first thing is to slow down enough to ask an honest question: what is the real problem we are trying to solve? Not “how do we implement AI?” but “what decisions are we making poorly, and why?” Not “how do we use these tools?” but “do we have the culture, the trust, the communication norms that would let us use any tool well?”

The second is to look at your leadership team with fresh eyes. Not at their AI literacy. At their judgment. At whether they are having the real conversations or the performative ones. At whether fear is running the room or curiosity is.

Kristi’s advice for getting grounded was simple: go talk to someone you trust who has no skin in the game. Not your board. Not your investors. Not the vendor selling you the platform. The colleague from ten years ago who always told you the truth. The mentor who is two levels ahead and has no incentive to flatter you. Your nine-year-old, who, as Kristi reminded me, is considerably more skeptical of AI than most executives.

Make your world smaller for a moment. The real signal is usually there, in the people who knew you before you had something to prove.

I am no longer scared of AI.

Well, that’s not entirely true. I am still fearful of the existential questions. But the day-to-day business implementations. I’m over that. AI is simply part of the evolution of business building.

What helped was not a course, a certification, or a deployment plan. What helped was getting honest about what I was actually afraid of. And then doing the work to address that, not the technology.

The fear was a signal. It was pointing somewhere real. The moment I stopped trying to bypass it and started getting curious about it, things shifted.

Your organization’s relationship with AI is telling you something about your organization. The question worth asking is not whether you’re ahead or behind. It’s whether you’re actually listening.

If this conversation sparked something, I’d love to hear what you’re navigating. Hit reply or share in the comments and tell me what the real conversation underneath your AI strategy actually is. The best ones always start there.

And if you are interested in understanding how to think about AI through the lens of a long-term strategist, not just a short-term tactician, subscribe to Kristi’s Substack — Systems & Spines and follow her on LinkedIn — trust me, you’ll be happy you did.

May you lead without limits,

In just under an hour, we covered something I have been thinking about ever since: AI isn’t exposing your organization’s weaknesses. It’s amplifying whatever was already there.

The great decisions get made faster. The poor ones do too. We talked about FOMO-driven boardrooms, the judgment-suppression risk no one is discussing, why the “point of decision” is the only unit of analysis that actually matters, and what it really means to lead with humanity in this moment.

Kristi also shared the personal story behind her pivot from two decades inside the machine to writing, teaching, and angel investing — and why she thinks the next generation of truly exceptional leaders will be the ones who can hold both their quant brain and their human one at the same time.

If you missed it live, here’s your guide to the conversation:

Timestamped Guide

• 0:00 Welcome and introductions

• 3:00 The central thesis: AI as a mirror, not a tool

• 5:00 AI as amplifier and accelerant — going faster in the wrong direction

• 7:00 The judgment-suppression risk and what it means for succession planning

• 10:00 What Kristi sees inside organizations right now: FOMO, board pressure, and the performance narrative

• 14:00 Why acting from fear almost never produces good strategy

• 15:00 AI as a path back to our humanity — the unexpected case for reconnection

• 19:00 OpenAI as a case study: when the “point of decision” goes wrong

• 21:00 Why judgment alone isn’t enough — and what the actual base unit of strategy is

• 25:00 The three intelligences: human, algorithmic, and artificial — and how to lead across all three

• 29:00 The limits of quant leadership and what AI is forcing us to reckon with

• 34:00 The next generation of exceptional leaders: holding the quant brain and the human one together

• 38:00 How to cut through the noise: slowing down as a competitive advantage

• 40:00 Kristi’s “humanity checker” and the case for trusted, low-stakes voices

• 42:00 The return of third places — and why shrinking your world might be the wisest move you make

• 47:00 Kristi’s career pivot: from the inside of the machine to writing, teaching, and investing

• 51:00 Why she’s considering teaching AP Physics and AP Calc to high schoolers

• 53:00 Angel investing, women founders, and seeing problems differently

• 57:00 What Gen Z already knows about AI — and the wisdom in their skepticism

• 58:00 Where to find Kristi: Systems and Spines on Substack and LinkedIn

Stay in touch with Kristi Pihl through her Substack: Systems and Spines and on LinkedIn.

I took the investment banking offer because I was afraid.

Not afraid of the job. Afraid of what would happen if I went after the one I actually wanted — and they said no.

The bank was platinum. Everyone wanted it. Saying yes felt like winning. What nobody saw was what I was using it to hide.

My fear. It was nearly all-consuming. Not just of interviewing, although the mini-panic attacks were bad. No, it was a deeper kind of fear.

I took the job because I was terrified that it was the only job offer I was going to get.

What if they had made a mistake? What if no one else would find me worthy of their ranks? What if the companies that I actually wanted rejected me?

I didn’t even know I was doing it, but I had let my fear win. I had let it trap me.

That was 25 years ago.

I went on to become a two-time CEO. The fear came with me.

Time doesn’t make the fear go away.

Going after what you really want, knowing that you could be rejected, that kind of fear doesn’t care about your age or your title.

It can find a way through, no matter where you are in your career.

Inertia is often fear in disguise.

“I know I should… but I just can’t,” he confessed with his eyes cast down, when I asked him why he hadn’t started networking.

I was meeting with a prospective client, a C-suite exec, who had just shared that he had known months ago that his current job wasn’t a good fit.

There was no path for growth, he was undercompensated compared to the market, and he didn’t enjoy the culture — all work, no play.

He knew he should be making a move, but couldn’t bring himself to start the process. After nearly 9 months, he finally reached out to me after his wife nudged him to get help.

I could hear the same rationalizations I made when I let my fear guide me. The time constraints and concerns about his resume, and worries about not knowing the right direction.

And then he paused and took a breath:

“I’m not sure anyone else will see what I have to offer.”

He looked at me, waiting for me to respond. Acknowledging it meant facing his fear. It was one of the most courageous statements I’ve ever heard from a leader.

There is something about the job search process that transforms everyone, even the most confident, successful leader, into a self-doubting, anxious, skittish person.

The judgment, the rejection, and these days, the ghosting.
It’s all too much.

The truth is, we’re all being evaluated in our jobs at every moment, but somehow, the quarterly targets or annual performance reviews create a facade that we are only on the chopping block a few times a year. The rest of the time, we breathe a false, but satisfying sigh of relief.

And so we stay — far longer than we should — in jobs that we’ve outgrown, in companies that drain us of our energy and our spirit.

Job searching is a special kind of torture.

For senior leaders who are used to being the decision-makers, the ones with the answers, the ones leading the charge for their teams, job searching flips the script.

From having the authority and the power to relinquishing both and becoming just another candidate who has to prove themselves and is at the beck and call of the hiring team — it’s a hard transition.

I get why so many leaders avoid starting the process (until they are forced to).

A two-time CEO and COO, and yet I was still plagued with the fears of my twenty-year-old self.

I was so scared of facing the unknown that I didn’t even realize I wanted to leave the company. That’s how fear works — it clouds your judgment, and it manufactures excuse after excuse to help you explain why.

Before you know it, days become weeks and weeks become months.

The job search doesn’t frighten people because it’s hard. It frightens them because it’s the one place where the thing that actually matters to them is on the line.

Worthiness. Belonging. Being chosen by the place that counts.

The fear brings you back to being eight years old. Waiting to be chosen for the kickball team. Answering wrong when the teacher called on you, the whole class watching.

These moments aren't weakness. They're just what it felt like to be human before you learned to hide it.

The secret to starting the job search process isn’t complicated.

It all starts with mindset.

The thing about a job search is that most people think of it the wrong way:

“I need to find a place that will hire me into the role I want with the pay I want.”

When actually, the right way to think about it is:

When you flip the script from “I need to find a way in” to “I need to help them find me,” you approach the process with a completely different attitude:

One of service instead of one of desperation.

In fact, when you use this approach, you realize it's less about letting go of your power and more about having the opportunity to be freed from the daily responsibility of thinking about everyone else instead of yourself.

Rather than worrying about all the people, processes, systems, tools — or what you do every day — you get to simply focus on what makes you incredible and what you can do to help an organization.

And instead of visualizing yourself running a gauntlet with hiring teams out to shoot you down, think of it as a chance to get to know organizations that need you.

You get to showcase your achievements, capabilities, and acumen, and be recognized for them. Unlike much of the rest of your work (and probably life), this entire process is about you.

Today, what I tell my clients is what I would tell my twenty-year-old self:

It’s not about taking a different job. It’s not about the job at all.

The fear you’re hiding from already knows where you live. Don’t let it keep you smaller than you actually are.

If this piece struck a chord, please consider sharing it with someone who you know will benefit. There are so many excellent leaders who are either out of work or wish they were, and are struggling with their next step.

If this can help just one of them, I would be so grateful.

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And if you are open to sharing your journey or a tip on how to get past the fear, the ick, the avoidance that holds up so many leaders from kicking off their search, I’d love to hear it.

Feel free to reply to this email (if you’re a subscriber) or add it to the Comments.

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May you lead without limits,

P.S. If you’re a leader who is thinking about what’s next, but you just aren’t sure. I’d love to chat.

I’m building something new for this fall. It’ll be a chance to step away from your day-to-day and give yourself the space to jumpstart your career.

If you want to learn more, send me a note. I’d love your input.

I came across a post he wrote in the Journal of Free Black Thought last year about what actually creates inclusion — not the slogans, not the frameworks with pretty acronyms, but the conditions under which real people genuinely contribute. And I thought: this person has done the work.

So I invited him to a Substack Live conversation. And I am so glad he agreed.

You can watch the entire conversation above or read the highlights below — the ideas I wish I had as a leader, and what I think every leader needs today. I’ve tried to organize them into themes, but if you want the full energy of the conversation, you need to hear Amri live.

Belonging vs. Mattering: Why the Difference Changes Everything

I’ve been in rooms — many of them — where someone was technically included. They were invited to the meeting. Their name was on the email. But their actual thinking, their particular expertise, the thing only they could bring? It was either overlooked or quietly ignored.

That’s belonging without mattering. And it turns out they are not the same thing.

Amri introduced me to a framework from researcher Zach Mercurio called NAN: Noticed, Affirmed, Needed.

• Noticed — Do you actually see the people around you? Do you notice what they’re working on, what they’re wrestling with, what they just accomplished?

• Affirmed — Can you articulate what someone brings to the table? Not a generic compliment. Can you specifically name their value?

• Needed — Do they know that without their particular contribution, the work is diminished?

The puzzle piece analogy is useful here: belonging is about whether the piece fits the puzzle. Mattering is about whether the puzzle needs that particular piece in order to be whole.

When you confuse the two, something goes wrong. I shared a story from my own time as a CEO. I remember sitting with my leadership team setting priorities, which every organization has to do.

The problem was never the priorities. The problem was how we communicated them.

We would, without quite meaning to, create a hierarchy of importance inside the company. Engineering was the most critical function right now — and somehow “most critical” became “most valued.” Everyone else could feel themselves shrinking. The sales team. The operations team. The people who were keeping things running.

That’s what Amri calls “anti-mattering.” And once it kicks in, the research is pretty clear about what happens: discretionary effort drops. Creativity drops. The willingness to ask good questions, share difficult observations, take risks — all of it goes down. People shift into survival mode. And survival mode is not the mode in which your next innovation gets built.

The Ubuntu Principle: Why Mattering Is Always Reciprocal

One of the things I appreciate most about Amri’s thinking is that he doesn’t let you stay comfortable in a top-down view of leadership. Mattering, he argues, is not something leaders dispense from above. It’s a reciprocal model.

He invoked Ubuntu: I am because you are. It’s the idea from post-apartheid South Africa, from Nelson Mandela and Desmond Tutu, that identity and value are not solo projects. They’re built in relationship. You cannot separate yourself from your organization and think you’ll build something great alone.

What this means practically is this: when you make people feel like they matter less, you are not just being unkind. You are making a strategic error. You are diminishing the part of your network that might hold the ideas you don’t yet know you need. You are cutting the “weak ties” — the people just outside your inner circle — who are, as Amri pointed out and the organizational network research backs up, often the source of the most surprising and valuable insight.

He told a story that made this vivid. A colleague of his at a major pharma company — a brilliant mind who had been quietly building an internal AI capability on the side, mapping who in the organization had machine learning skills and who was just beginning to explore them — was being ignored by his manager. The manager didn’t understand what he was building. Didn’t see its value. Eventually, his manager put him on a performance improvement plan.

Amri’s colleague left. Went to a competitor. And became one of the leading AI architects in the Cambridge biotech ecosystem.

His company lost him because no one could see what he brought.

The story is about more than a bad manager. It’s about a system that wasn’t designed to notice the right things. And systems, Amri reminds us, create behavior. Structure creates culture. If your incentive structures reward individual output over collective contribution, you shouldn’t be surprised when people optimize for themselves.

The “DEI-Allergic” Leader — and Why This Conversation Is for You Too

Amri and I deliberately named this conversation, “Mattering for the DEI-Allergic.” And yes, it didn’t land for everyone.

Some people were frustrated by the framing. I understand that. I want to address it directly, because the frustration itself is instructive.

The allergy, Amri argued, was never to the underlying principles. Nobody looks at a room full of people who are contributing brilliantly, being genuinely seen for what they bring, and says: I want less of that.

The allergy was to the way the conversation was framed — often as a moral debt to be paid, with slogans in place of substance, centering group identities and grievance above all else, and with equity defined so broadly it became operationally meaningless.

Amri was clear: he wouldn’t have put DEI on the cover of his book if it hadn’t been in vogue at the time. He would have called it inclusion. Because that’s what he actually believes in — creating the conditions for people to thrive, and for organizations to generate what he calls “thick value”: the return on intangibles that don’t show up on your P&L but absolutely show up in your valuation, your ability to retain talent, and your capacity to build anything new.

Mattering is a different entry point into the same territory. It doesn’t ask anyone to take a political position. It asks: Does this person know what they bring? Do they know we need it? Are we building the systems that let that show up?

That’s not soft. That’s strategic.

The Structural Reality: How Leaders Actually Create (or Destroy) Mattering

Here’s what I will hold onto going forward: mattering is not a feeling you inspire with a good speech. Mattering is a condition you build — or fail to build — through the decisions you make every day.

Amri put it simply. Structure is a set of behaviors that creates a different tenor or condition for others to mirror. When your direct reports see you notice the person two levels below you and write them a specific, handwritten note about something they did well — that becomes a norm. Norms become rituals. Rituals become culture.

He made the point about senior leaders writing personal notes — not email, not Slack, but actual notes, four or five a week, to people outside their direct report line. When they see something, they write it down. Then they send it. He calculated: if you do that two or three times a week, times 52 weeks — you’ve touched over 100 people with a specific, genuine act of recognition.

That’s structure. Most people wouldn’t call it that. But it is.

I shared some of my own limitations here, and I want to be honest about it. When I was a CEO, I wanted to create the conditions where people genuinely mattered. I didn’t always have the language for it, but that was the intent. And then the sales pipeline would fall behind, or the marketing campaign would stall, or we’d be in the middle of building out an entirely new evaluation system, and the intention would get crowded out.

Looking back, I don’t think it was entirely an intentionality problem. It was partly a knowledge problem — I didn’t have the specific, concrete tools that Amri gave me in this conversation. And partly it was a capacity problem. I couldn’t do everything.

So I asked him: What does the overwhelmed leader actually do? And he said, without hesitation: One thing. Consistently.

Pick one behavior. Do it every week. Let it become a habit. Ask your direct reports to do the same. Let the habit become structure.

It’s not complicated. But you do have to commit.

The Ask as an Act of Mattering

I love this one. I first learned about it as a trust-building exercise from David Brooks in his book, How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen. It still blows my mind.

Asking someone for help — genuinely asking, not assigning, not delegating, but saying “I’ve been wrestling with this, what do you think?” — is itself an act of mattering.

Amri connected this to Marshall Goldsmith’s Feed Forward practice: instead of giving feedback on what happened, you ask for input on what you’re thinking through. There’s no evaluation involved. Just: here’s a direction I’m considering, what do you see?

It works, Amri said, because it gives people the opportunity to add value without judgment. And when people add value, they feel like they matter. And they do because their input adds to your thinking. It’s a loop. A good one.

The same logic explains why research indicates that employee volunteering is the only employee benefit outside of healthcare that truly makes a difference in employee engagement. Once you understand mattering, it’s obvious.

Volunteering is one of the cleanest expressions of mattering that exists: you contribute based on your choice, you see the direct impact, and you do it as a whole person, not a job title, and if you do it with your colleagues, you’re seeing the power of collective work. Of course, it moves the needle on engagement more than free lunches or office massages. It’s the one benefit that is entirely focused on people mattering.

Timestamp Guide

If you’d like to go straight to a specific section of the conversation, here’s where to find it:

00:00 — 04:00 | Opening: Introductions and frames the “DEI-allergic” framing
04:00 — 15:15 | Amri’s background: Topeka, Morehouse, epidemiology, Atlanta, Cook Ross, and how he got into this work
15:20 — 19:30 | The mattering construct: where it comes from, how it differs from belonging
19:30 — 23:00 | Noticed, Affirmed, Needed — the NAN framework
23:00 — 28:00 | Ubuntu and interdependence; how anti-mattering cascades through an organization
28:00 — 36:00 | Layoffs, weak ties, and the story of the AI genius who was lost
36:00 — 41:30 | Incentive structures: what happens when rewards don’t align with mattering
41:30 — 45:00 | The “DEI-allergic” framing unpacked; what the allergy is really about
45:00 — 49:00 | Volunteering research; asking for help as an act of mattering
49:00 — 53:00 | What the overwhelmed leader does: one thing, consistently
53:00 — 58:34 | Closing: Amri’s resources and where to find him

Stay Connected with Amri Johnson

If this conversation sparked something for you, Amri’s thinking goes much deeper than one hour could cover.

On Substack: Find him at Reconstructing Inclusion.

On LinkedIn: Amri Johnson

His book: Reconstructing Inclusion: Making DEI Accessible, Actionable, and Sustainable — worth your time if you want the full framework, not just the highlights.

His company: Inclusion Wins, at inclusionwins.com. He runs a course on building the mattering habit — practical, structured, something you can start immediately. If you’re a leader who wants specific tools, not just concepts, it’s a good place to start.

I met Amri on Substack. This was his first live. I will not forget it — and I hope you won’t either.

And if our conversation landed for you, consider sharing it with a friend or giving it a ❤️. That will help more people access these valuable insights.

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May you lead without limits,

“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.

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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.

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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?

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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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