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,

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

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,

Welcome to Lead without Limits where I share unvarnished truths and actionable tips each week to help you traverse the often difficult terrain of work and life with more joy and energy.

Last week, I had the privilege of hosting Molina-Shaefer for a Substack Live conversation that left me thinking bigger, dreaming bolder, and reconsidering what’s possible in my own career. Maia’s journey -- from boxing ring to combat zones, from military diplomat to nonprofit leader --offers a masterclass in navigating career transitions while staying anchored to your core purpose.

If you’ve ever stood at a career crossroads, wondered whether you’re “qualified enough” to make a leap, or struggled to maintain your identity through major transitions, this conversation is for you.

The Power of “Challenge Accepted”

Maia’s path to the Naval Academy didn’t follow the script she’d imagined. Despite being recruited for sports by multiple colleges and submitting what she thought was a strong application, she was rejected.

“It was a huge surprise and a shock to me when I actually didn’t get accepted. I wasn’t really used to being rejected or someone telling me, you’re not good enough to come to our school.”

Instead of internalizing that rejection, Maia used it as fuel. She spent an extra year at a foundation school, focusing on STEM courses, and reapplied. The second time, she got in.

Here’s what strikes me about this: Maia didn’t just persist blindly. She took that “no” as information. She identified what needed strengthening, invested the time to build those skills, and came back stronger.

Your Takeaway:
When you face rejection or a setback, ask yourself: Is this a hard stop, or is this feedback about what I need to develop? Sometimes the path to where you want to go requires a detour that actually makes you more prepared for what’s ahead.

Leading Through Listening

One of the most powerful themes in our conversation was Maia’s approach to leadership in unfamiliar contexts. When she arrived in Niger as the first woman to serve as Chief of Office Security Cooperation, managing a $240 million portfolio, she faced what many of us fear: being underestimated because of who we are.

“I was really worried that my gender was going to be my vulnerability. I thought it was going to be something that prohibited me from entering rooms that my predecessor had automatic open doors to.”

Instead of trying to prove herself through force or directness, Maia led with curiosity:

“I would sit down with them. I’m like, please tell me, what is your vision for your defense force? What do you think your capability gaps are? What do you think your strengths are? How can we as partners help you get there?”

The result? What she thought would be her weakness became her superpower. By listening first, she gained access to both the male military leadership and the women within the defense force, perspectives her predecessors couldn’t reach.

Your Takeaway:
When you step into a new role or environment where you feel like an outsider, resist the urge to immediately prove yourself. Instead, ask questions. Listen deeply. The trust you build through genuine curiosity will open more doors than credentials alone ever could.

SAVE THE DATE: Monday, December 22nd at 10am ET for a live conversation with Aamina Awan-Khan on “The Intersection of Identity and Purpose.” Aamina was the former Chief Partnerships Officer in the U.S. Department of State’s Bureau of Public Diplomacy and has held management roles with the Clinton Foundation, the United Nations and Credit Suisse AG. (Link to join)

The Identity Shift No One Talks About

One of the most vulnerable moments in our conversation came when Maia talked about switching from the Marine Corps to the Army after 10 years of service:

“I was really worried that when I took that name tag off that I wouldn’t know who I was. I had spent my entire career being a Marine officer, training to be one, hitting the highest standards to be as best as I could. And I loved being a Marine.”

This resonated deeply with me. I’ve witnessed so many leaders struggle with similar identity shifts: leaving a prestigious company, transitioning from corporate to nonprofit, stepping away from a title they’ve worked decades to earn.

But here’s what Maia discovered: “When I put on that Army uniform, I was like, oh, I’m exactly the same. Like actually nothing has changed about me.”

The uniform changed. The organization changed. The culture changed. But her mission, to serve her country, create opportunities for others, and lead with integrity, remained constant.

Your Takeaway:
Your identity isn’t your title or your organization. It’s the mission you’re committed to and the values you bring to every arena. When you’re clear on those, you can step into new contexts without losing yourself.

Communication Isn’t One-Size-Fits-All

Throughout her career, Maia has had to radically adapt how she communicates: from briefing generals in combat zones to negotiating with foreign military leaders in French to now working with nonprofit leaders in New York City.

She shared a funny example from her current role: “I will teach them a military term a week… I’ll walk in and say, OK, what’s the closest alligator to the boat? And they [respond with confusion in their eyes], what are you talking about?”

This isn’t just about learning new jargon. It’s about recognizing that effective leadership requires meeting people where they are, speaking in language that resonates with them, and being humble enough to ask when you don’t understand. And it means being willing to share the context of your language, too — that’s how you create authentic connection.

Your Takeaway:
As you move between contexts, whether that’s different departments, industries, or cultures, pay attention to how people communicate. What metaphors do they use? What matters to them? Your ability to translate your experience into their language will determine whether your expertise lands or falls flat.

The Myth of Being “100% Ready”

Near the end of our conversation, I asked Maia what she’d say to someone considering a big career leap. Her response was immediate:

“I feel, especially as women, we feel that we can’t take on a new opportunity or do something new unless we’re 100% prepared and ready to go. And I would say that a lot of these jumps that I took in these different arenas, I was not 100% ready to go, right? But I knew that once I got in there, I could learn.”

This is the permission slip so many of us need. We wait for certainty that will never come. We wait to feel completely qualified. We wait until the fear disappears.

Maia’s advice? “Comfort is the enemy of growth.”

She reminds her son daily:

“You have survived 100 percent of your hardest days.”

If you’re like me, you needed to hear this. I’m keeping this one on my “revisit weekly” list.

Your Takeaway:
Stop waiting to feel ready. If the opportunity aligns with your mission and values, if you’re willing to learn and have a support network to lean on, take the leap. The growth happens in the arena, not on the sidelines.

Building Trust Takes Time (and That’s Okay)

One insight that particularly struck me was Maia’s patience in building trust, whether with her diverse team in Niger or with military partners who weren’t used to working with a woman in her role.

“Trust, confidence and respect. It takes a lot of time to build that. And it comes with results. You have to prove yourself always.”

In our efficiency-obsessed culture, this can feel frustrating. We want to be direct, get to the point, make things happen fast. But Maia’s experience shows that sometimes the “efficient” path actually takes longer if people aren’t ready to trust you yet.

Your Takeaway:
When you step into a new leadership role, especially one where you’re breaking new ground, build trust before pushing for change. Show up consistently. Deliver on what you promise. Listen before you advocate. The relationships you build will determine what you can accomplish.

Translating Your Skills Across Arenas

Maia’s transition from military service to nonprofit leadership required more than just finding a new job. It required translating 20 years of experience into language and context that made sense in a completely different world.

“For veterans that are transitioning out of uniform, it’s really important to be able to translate your skills. We’re really good at listing off our technical capabilities... But that doesn’t work really well when I’m in a room full of nonprofit leaders.”

This applies to all of us navigating career transitions. Your skills are transferable, but you need to reframe them for your new audience.

Your Takeaway:
When making a career transition, don’t just list what you’ve done. Articulate what you’ve learned, how you think, what problems you solve, and how that applies to the new context. Your past experience is valuable. But only if you can help others see its relevance to their world.

Finding Your Mission, Not Just Your Next Job

What made Maia’s conversation so powerful wasn’t the impressive resume or the list of “firsts” she’s achieved. It was her clarity about her mission: creating pathways for others, serving with integrity, and being the best leader she can be while staying true to her values.

That mission has remained constant whether she was:

• The first woman to compete in the Naval Academy’s brigade boxing championship

• Managing a $240 million security cooperation portfolio in Niger

• Teaching at West Point

• Investing in women and girls as changemakers in New York City

• Building a speaking and storytelling portfolio

The arenas changed. The mission didn’t.

Your Takeaway:
Before you make your next career move, get clear on your mission. What are you ultimately trying to accomplish? What impact do you want to have? When you’re anchored to that, you can evaluate opportunities not by title or prestige, but by alignment with what matters most to you.

Your Next Move

If you’re considering a career transition, feeling stuck in your current role, or wondering whether you have what it takes to step into a bigger arena, I want you to sit with this question:

What is your mission? Does it need to change or do you need to change the arena?

Before you worry about your job title, your industry, your specific role, clarify your purpose. It will be your guide as you figure out what needs to change and be your an anchor when everything else shifts.

For Maia, it was creating pathways for others and leading with integrity.
What is it for you?

And once you know that? As Maia says: “Be bold. You just never know what is going to happen unless you take that leap and you jump into it.”

You’ve survived 100% of your hardest days. You’re ready for the next arena.

If you felt inspired by her story and want to stay in touch, connect with Maia on LinkedIn or visit her at voiceinthearena.com

What resonated most with you from this conversation? Hit reply and let me know. I read every response.

Leave a comment

Conversation Topics & Timestamps

Introduction & Background (00:00:00 - 00:05:10)

• Maia’s journey from boxing to military service to nonprofit leadership

• Growing up with a single mother in Buffalo, NY

• The value of hard work and education instilled early

The Naval Academy Journey (00:05:10 - 00:09:00)

• Being recruited for sports but initially rejected from the Naval Academy

• Using rejection as fuel: attending foundation school and reapplying

• Learning that persistence paired with strategic preparation opens doors

Boxing & Breaking Barriers (00:09:00 - 00:11:45)

• Why boxing after 9/11: building physical and mental resilience

• Becoming the first woman to compete in the brigade boxing championship

• Petitioning for change and creating pathways for women who follow

First Combat Deployment (00:11:45 - 00:14:30)

• Leading Marines in Iraq at age 22-23 for 15 months

• Focusing on the team’s preparation rather than personal fear

• Learning to put people first as a leadership principle

Becoming a Commanding General’s Briefer (00:14:30 - 00:19:12)

• The power of being a good communicator and knowing your audience

• Transitioning to aide-de-camp: shadowing C-suite level decision-making

• How mentorship and sponsorship opened doors to become a Foreign Area Officer

Becoming a Military Diplomat (00:19:12 - 00:24:00)

• Three years of training: master’s degree, learning French and Kiswahili

• Traveling to 25 African countries to understand the landscape

• How early opportunities create ripple effects throughout your career

Switching from Marines to Army (00:24:00 - 00:30:05)

• The identity crisis of taking off the Marine Corps name tag

• Realizing the mission stays the same regardless of the uniform

• Balancing professional goals with personal life and family

Leading in Niger (00:30:05 - 00:41:00)

• Managing a $240 million security cooperation portfolio

• Turning perceived vulnerability (being a woman) into a superpower

• Leading with listening: understanding your partners’ vision first

• Pioneering the first Women, Peace, and Security program

• Building trust through results and authentic partnership

Communication & Cultural Intelligence (00:41:00 - 00:45:00)

• Adapting communication style across diverse teams

• Leading with emotional intelligence and empathy, not just directness

• The importance of timing in negotiations and relationship building

Transition to Education (00:45:00 - 00:46:30)

• Teaching at West Point as a highlight of military career

• Mentoring the next generation with the knowledge she wished she’d had

Retiring & Joining Nonprofit World (00:46:30 - 00:52:00)

• Choosing purpose over profit after retirement

• Finding Amplify Her Foundation: investing in women and girls in NYC

• Translating military skills to nonprofit language

• Learning to be humble and curious in a new arena

The Power of Storytelling (00:52:00 - 00:55:00)

• Why storytelling matters: combating bias and creating connection

• Representing female veterans and changing perceptions

• Finding joy in unexpected places through shared stories

Advice for Taking the Leap (00:55:00 - 00:57:23)

• You don’t need to be 100% ready to make a move

• Comfort is the enemy of growth

• “You have survived 100 percent of your hardest days”

• The importance of doing something scary and trusting yourself

If you found this post valuable, consider clicking to leave a ❤️ so more people can discover it on Substack.

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I feature leaders each month in conversations just like the one I had with Maia. If you know of a leader or are one yourself that would be interested in having an open and honest conversation about your experience and expertise, please email me or send me a DM.

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May you lead without limits,

Alex has quickly become one of the most thoughtful new voices exploring how work and identity are evolving.

His viral essay “The Death of the Corporate Job” struck a deep chord across generations — surfacing something many people have quietly felt: that the traditional corporate path no longer guarantees fulfillment, stability, or even belonging.

Our conversation explored what comes after that realization — and how to design a career that actually fits the life you want.

Here are a few of the themes we unpacked together:

The power of a beginner’s mindset.
Alex shared how being early in his career has been an unexpected advantage. By leading with curiosity and empathy rather than expertise, he’s building a body of work around listening deeply and spotting patterns in others’ career struggles.

A beginner’s mindset has served me my entire career. It’s what enabled me to shift from industry to industry and function to function.

In this next era of work, careers are going to look even more fluid and dynamic. Having a beginner’s mindset is what will allow you to navigate the change.

—

The loneliness of career transition — and why community matters.
We talked about how uncertain career moments can feel isolating, especially when so much of our identity is tied to our job title.

Alex’s Midweek community was born from that insight: the idea that clarity comes not from thinking harder, but from talking, testing, and being held accountable by others who understand.

When we are unsure, it might feel safer to stay quiet, but the opposite can be true. Conferring with and communing with others can help us find our way.

—

You can’t think your way to clarity.
Both of us have seen how important it is to act your way into knowing — through experiments, conversations, and creative exploration.

It’s how I discovered writing and launched my coaching practice after two decades of corporate leadership, and it’s how Alex is helping people uncover meaningful next steps through True North.

Taking a step forward is the only way to discover what is right for you, over and over again throughout your career.

—

Adopting an entrepreneurial lens — without needing to be an entrepreneur.
We explored the idea that every professional can think more like a builder: identifying problems worth solving, testing ideas, and aligning your skills and passions with what the world actually needs.

It’s not about quitting to start a company; it’s about reclaiming agency and designing your next chapter intentionally.

Entrepreneurs don’t wait for someone else to define the problem and propose a solution. They don’t need permission to dive into the work. They combine an owner’s mindset with a doer’s mindset.

Anyone can do this. And now more than ever, the professionals who will have the most fulfilling careers need to adopt this approach.

—

Rethinking identity and worth.
We shared personal stories of what it feels like when a title disappears, and how to rediscover your worth beyond your role.

Culturally, Alex and I both have lived in societies where you can’t spend more than a few minutes with someone before they (or you) inevitably ask, “What do you do?”

It’s an innocuous question on the surface. But beneath the question is layer upon layer of assessment about status and power. And it generally results in two people exchanging superficial and limiting labels: job titles.

What’s even more sad than the label is how we become attached to them. I spoke about the panic I once felt when I knew my executive job was ending.

The C-level roles I hadn’t sought out had become part of my identity, a symbol of my worth. It was a significant shift to reclaim my full self. It was difficult, and it was an opportunity to rebuild my narrative.

—

Why this conversation matters

Whether you’re at the start of your career, mid-journey, or somewhere between reinvention and rest, this conversation is a reminder that your career should fit your life — not the other way around.

If you’ve been feeling restless or uncertain about what’s next, I think you’ll find Alex’s perspective grounding and hopeful.

I’d love to hear what resonates most for you — drop your reflections or questions in the comments.

More Lead without Limits Substack Live’s

Recorded
Leading Through Fire: What I Learned from Former FDNY Commissioner Laura Kavanagh (Watch it here)
Our conversation delved deep into what it takes to lead through change and crisis, and her reflections on leading a 17,000 person, $2.3 billion budget major public service institution.

Upcoming
Tuesday, November 18th at 11am ET with of Sense Labs. Paul is a former Chief Strategy Officer and the author of MAGNETIC NONSENSE: A SHORT HISTORY OF BULLSH*T AT WORK AND HOW TO MAKE IT GO AWAY. We’re going to talk about Dysfunction at Work. Is It The People Or The System? Join us!

Call for Topics & Speakers
Is there a topic you’ve been hoping I would cover?
Is there a person I should be hosting on a Lead without Limits Substack Live?
DM me or reply to this post. I want to hear your recommendations.

Thanks for joining me this week!

May you lead without limits,

Special Announcement: Join me for a Substack Live today, November 4th at 11am ET with Alex McCann of Still Wandering. We’re talking about how to evolve your career to fit your life. (Link to join)

“Ouch.”
The nurse pierced the same vein for the fourth time.

I was 22 — just nine months out of college — and stuck in a chair for six hours of blood sugar testing.

I had ballooned 40 pounds in under a year.
High cholesterol. High triglycerides (that’s fat, by the way). No period.

I felt like the Stay Puft Marshmallow Man.

My body thought I was pregnant.

I wasn’t.

I was just very, very sick.

And none of this… was in the plan.

It wasn’t part of the plan.

I was 22 years old, having achieved everything I was supposed to, and deeply miserable.

It was the first of many life curveballs that challenged my notion of success.

What matters.
What doesn’t.

High achievers are taught to aim for clear goals.
Hit one milestone, climb to the next. Repeat.

But here’s the part no one prepares us for:

Your body doesn’t follow your plan.
Your family doesn’t.
Life doesn’t.

And when things go sideways — really sideways — that’s when the most successful people get thrown.

Not just distracted. Shaken. Unsteady.

Why?

Because you’re used to being in control, setting the pace, and hitting your marks. I know I was.

Getting sick at 22 was one of the best things that could have happened to me.

Here’s why.

(Re)learning how to prioritize what actually matters.

I thought landing one of the most coveted jobs in a competitive industry meant I’d “arrived.”

It didn’t.

It was the end result of a decade of playing it safe.
Following paths carved by people I didn’t know.
Not trusting myself.

When you choose a direction that isn’t right for you, there is only one result: Stress.

Even if your head can’t admit it — your body will always tell the truth.

Mine did. Loudly.

Here’s what it said:

• High, constant stress → I was scared I’d get fired every day

• Severe lack of sleep → I was working 18–20 hours a day, 6 days a week

• Poor diet → 3,000–4,000 calories a day just to self-soothe

• Mild depression → I felt trapped in the “dream” I had worked so hard to build

No one was mistreating me.
No toxic boss. No hostile environment.

It just wasn’t the right fit.

And still — it took me months to admit it.

I didn’t take action until my bloodwork screamed at me.

It took leaving that job, moving home, and 2 years of a completely different lifestyle to regain my health.

It was the beginning of learning to choose myself.

I stopped outsourcing my direction.

I started making career choices based on my compass.

It’s how I ended up traversing media, e-commerce, and social impact. Every change brought critique and baffled former colleagues.

That was OK.
I wasn’t making my decisions for them. I was making them for me.

I thought getting sick in my twenties was the hardest curveball I’d face.

It wasn’t.

That was just the warm-up.

Parenthood cracked me wide open.

Fertility treatments. Chronic nausea. All the “fun stuff” women rarely talk about in boardrooms.

But the real blow came after the babies arrived.

My kids have each suffered severe sleep anxiety that lasted for years: 5+ years for my son, and 2+ years for my daughter.

Eight years. Back to back.
Those years were hard.

I wasn’t just tired, I was frequently ill, emotionally drained, and mentally foggy.
All of this happened while I occupied executive posts with large, complex mandates.

People’s jobs were dependent upon my ability to lead.
I felt that responsibility daily.

And yet, I was breaking out in hives from the stress of holding it all together… barely.

Eventually, I took a step back, descoped my role, and took a salary cut, all with the hope of reducing my stress.
That was fall 2019.

And then… well, you know.
2020 arrived.

So much for good intentions.

Coupled with a global pandemic, 3 out of the 6 executives in my company took 4 months of parental leave — each.

I didn’t begrudge them their time and still don’t. But the reduction in work I had thoughtfully planned? It never materialized.

Emergency after emergency came up.

Every temporary coverage plan turned into another temporary plan. What was supposed to be a time of reprieve became a four-year stretch of treading water.

And yet, similar to my illness at the beginning of my career, I needed this to happen to realize what I truly wanted.

I thought start-up leadership was my forever lane.

I thought I’d stay until retirement.

But it took a crisis — one that wrecked my health, strained my marriage, and tested my sanity — to see the truth:

I was done.

When my role was eliminated in January 2024, I felt clear.

Not devastated. Not lost.

Ready.

I took a sabbatical.
Launched the coaching practice I’d dreamed of for nearly two decades.
Picked up my paintbrush — something I hadn’t done in 35 years.

None of that would’ve happened if I hadn’t been cracked open first.

The curveballs — the ones that wrecked my health and blurred my sense of self — gave me space to imagine a new chapter.

A chapter where I live in alignment.
Where I help other leaders do the same.

I don’t know what the third curveball will be. But I know it’s coming.

Life tends to deliver in threes.

I don’t wake up dreading it.
But I do expect it.

And when it arrives — like the ones before — it will bring hard-won gifts.

Painful, yes. But clarifying.

Because when we stop resisting the hard things, we start making decisions that are aligned with what actually matters.

If you’re navigating your own curveball and wondering what it might be here to teach you — I see you.

I coach senior leaders through these exact moments: where your body says “no,” your calendar says “more,” and your soul is quietly asking for a different kind of success.

And if you’re ready to talk about what’s next for you — I’d love to connect.

Book a Free Strategy Call

If you feel like sharing, drop a comment or email me privately. Sometimes just saying it lightens the load.

And if this story spoke to you…
Pass it along to someone who might need it today.

If you’re new here, subscribe to get weekly reflections and strategies for leading well, living well — and building a career that fits your actual life.

Subscribe now

I also host regular Substack LIVE sessions where we talk career evolution, leadership power moves, and finding clarity in chaos.

• Today, November 4, 11am ET: Evolving Your Career Path to Fit Your Life with of Still Wandering. (Link to join)

• Monday, November 10, 11am ET: Join me for a conversation with the former Commissioner of the NYC Fire Department, (Link to join)

• Tuesday, November 18, 10:30am ET: Join me for a conversation with from Sense Labs (Link to join)

Looking forward to seeing you there!

May you lead without limits,

Until a few months ago, my relationship with AI was one of avoidance and shame, accented by images of the Terminator and Wall-E.

It made no sense. I helped launch Hulu. I built my first website in ‘96. I even convinced my friends to buy OLED stocks before it was cool (and profitable).

But life happened. Parenting. Burnout. Too many to-do lists. And slowly… I drifted away from the tech world I once loved.

What brought me back wasn’t hype or headlines.

It was something way more human.

Here are the 7 mindset shifts that helped me face my fear—and find my edge again.

#1: Set the right expectations (for you)

I used to think I had to “know it all” to be worthy of engaging with AI—especially as a former C-Suite leader.

That belief crushed my curiosity.

I put off exploring because I was afraid to fail publicly… or even just suck at something new.

Only when I reset my expectations this past year did I finally create the conditions to feel safe enough to dabble in AI.

It was all part of the context I set for myself in building my business.

I told myself to “simply enjoy the experience and take small steps forward every week.” I didn’t set stretch goals. I wasn’t aiming to help 1 million people. I wasn’t trying to build a 7-figure business.

Aiming high isn’t bad, but don’t do it because someone else says so.
That’s a recipe for burnout.

Set expectations that match your needs.

“The chief problem in self-improvement is that people’s desire to be more worthy puts tremendous pressure on them, so that their first efforts, if unsuccessful, create a feeling of failure, and they give up”.
― B.J. Fogg, Tiny Habits: The Small Changes That Change Everything

I started with using ChatGPT to help me with my branding, outlining my target customer and my offering. Then I tried out various custom GPTs to help me improve my writing.

I viewed most of my interactions with skepticism, but I could see the value of AI even in a few brief interactions.

I was slowly rewiring my brain to find a way to engage without fear because I had finally set the right expectations.

—

My takeaway:
Set expectations that serve your growth, not your ego.

—

#2: Don’t go it alone

When you’re in burnout mode, isolation feels like a safe place.

But it’s not.

In school and at companies earlier in my career, I was always surrounded by people curious and excited about technology. I was never the most knowledgeable and I didn’t have to be.

This year, I started reaching out again. Old friends, former colleagues… people I respected but hadn’t spoken to in years.

That’s how I ended up at the OverdriveAI conference. With my friend Mark from our Hulu days.

Reconnecting reminded me: community isn’t optional—it’s essential. Especially in tech.

You don’t need to be the smartest in the room. You just need to be in the room (again).

This last Thursday, we met in real life at Nokia Bell Labs at the TechUnited OverdriveAI Summit.

It had been more than a decade since I had attended a conference where tech was the theme. I was nervous.

It ended up being the best half-day I had experienced in months. The speakers were engaging, sharing hard data and raw truths.

They didn’t dispel all my fears about AI, but they did help me see new possibilities. And they changed how I believe I need to engage with AI going forward.

I don’t need to do more with AI.
I need to stop working with AI alone.

The power of collaboration, sharing knowledge (and misses), and problem-solving together is essential to any innovation. I knew that, but had forgotten in the haze of the last few years.

—

My takeaway:
Collaboration beats isolation. Every time.

—

#3: Trial and error is the only way

Mano Mannoochahr, Verizon’s Chief Data, Analytics & AI Officer, shared that they have deployed over 1,000 AI models, including:

Reviewing and analyzing customer bills, guiding customer service representatives on next actions on live calls, and even creating a podcast for managers to hear a digest of the top call center issues weekly.

Verizon didn’t build these by staying still. They are constantly testing and learning.

Dan Van Tran shared how Collectors, a billion-dollar business built on valuing and trading sports and Pokemon cards, ran a test that went sideways and set them back a year.

What did they do?
They got back at it and kept going.

Anthropic recently ran a test to see if AI could run a small business of vending machines within the company. AI ended up making up customers, denying the mistake and saying it was an April Fool’s joke.

The test was a failure, and they celebrated the learnings.

AI is like any other major shift: You figure it out by doing, not by waiting for it to be perfect.

—

My takeaway:
Don’t wait for mastery. Get your hands dirty and learn as you go.

—

#4: Think revolution, not optimization

Most of us are asking:
“How can I use AI to be 10% faster?”

That’s the wrong question.

The right one is:
“What would my work look like if I started from zero… and built it with AI from day one?”

• Technology teams are shifting from 2-week sprints to 2-day sprints.

• AI native startups are going from no product to $$M in revenue in 6 months, not 6 years.

• AI is enabling traditionally analog services, like law firms, 4x margins

• Revenue efficiency is dramatically different for AI companies compared to traditional tech:

Because the real wins aren’t tweaks—they’re reimaginings.

There are risks, but the opportunity to leverage AI is astonishing, if you’re willing to dream it.

—

My takeaway:
AI isn’t a tool to help you move faster. It’s a partner to help you do things differently.

—

#5: Redirect your expertise

Working with AI is like working with 10,000 interns.

- Barclay Blair, Senior Managing Director of AI Product Innovation at DLA Piper

AI doesn’t “know” anything. It only knows what you feed it. And while that means it will get “smarter” over time, the wrong way conclusion to draw is that your career is over.

The right conclusion is that it’s time to prepare to pivot.

Leaders with depth are positioned very well to win in the age of AI. But only if you are ready to adapt.

Ethics, judgment, expertise, and relationships are the areas that AI cannot tackle on its own. If you possess these, you have the advantage.

Here’s how to put that advantage to use:

• Know when to use AI and when not to. Only use AI when you can properly direct and assess its output. When you are still learning and need to build your expertise, don’t rely on AI.

• Learn how to mold AI to your needs. Learn how to prompt effectively. Not just the initial request, but the determination and persistence needed to hone AI output into what is actually valuable.

• Help AI companies build expertise. Instead of waiting to be replaced, be the one helping to educate AI. (Example: AI companies are recruiting financial analysts to work less and integrate their expertise.)

• Zero in on work that only you can do. Your “zone of genius” will have only more meaning in the future. What you do uniquely well, that you enjoy, is in demand, and cannot be replicated by AI, is going to matter more than ever.

To be clear, those who don’t pivot risk being left behind and worse, being left out of the evolution. But the great news is that AI access and knowledge are nearly ubiquitous.

From Youtube to Github, from podcasts to the multitude of models available, there are plenty of ways for you to get your feet wet.

No technology change has yet to shrink the labor pool. However, there will be winners and losers.

—

My takeaway:
AI doesn’t have to replace you. But you do need to reposition yourself.

—

#6: Build bridges, not barriers

AI can only improve with the guidance of humans and the data we feed it. This means that there is an entirely new layer of roles that is entirely focused on connecting the dots between AI and what it is capable of delivering

Mike Wilner who heads GTM Startup relationships for OpenAI shared a list of some of the new engineering jobs that are emerging as an example:

• Internal Context Engineers — They refine the prompts and the information that helps AI get to better results.

• Machine Learning and AI Engineers — They run the experiments and assess the outcomes to determine what inputs and interpretations need adjustment.

• Forward Engineer (pioneered by Palantir) — They provide services deployed on-site at clients. Forward deployment doesn’t just help with client integration; it provides critical information to the development teams that wouldn’t be available without on-the-ground context.

• Go to Market Engineers — They power the tech stack necessary to optimize marketing and sales to reach the right customers and increase conversion efficiency.

We have lived in a world where we thought first about roles and then about people. With AI, a completely new model emerges.

Now we can start with “how much can AI do,” and then add in “where do you need humans in the loop?”

The key is to be able to take a systems-level view of the work at hand and see it across functions and roles. The connection points are where the power lies.

Those who understand this and pull together the people and processes will make the greatest impact. Those who build up barriers will be left behind at best and exited at worst.

—

My takeaway:
Stop thinking in silos. Start thinking in systems.

—

#7: Proximity matters

Remote work isn’t going anywhere. But if you want to lead in AI, being around the action matters.

• Talent: Functions and skillsets density (e.g. NJ is strong in engineering)

• Customers: Verticals and industries concentration (e.g. NJ has pharma, finance, accounting, manufacturing, logistics)

Location shapes access. Relationships deepen in person. Innovation thrives in collisions.

AI isn’t in the cloud. It’s in conversations.

—

My takeaway:
Get in the room. Or build a new one where you are.

—

Closing thoughts (for now)

I avoided AI because I was afraid of losing relevance.
But what I’ve realized is this:

The way to stay relevant isn’t to master AI. It’s to keep evolving—with people, with courage, with intention.

That’s what this year gave me.
That’s what I want to help others do.

If you’re trying to make sense of your next chapter in leadership or career…
I’m here.

If you want to join me on this journey, leave a comment, subscribe to this newsletter, or follow me on LinkedIn.

We will get there together!

✨ Final takeaway:

The future doesn’t belong to those who know it all. It belongs to those willing to stay in the game and keep learning.

If you want more from me, Save the Date!

My next Substack LIVE is on Tuesday, November 4th, with , the thoughtful and viral author of Still Wandering and founder of TrueNorth and MidWeek. We’re talking about how to evolve your career to fit your life.
Join with this link.

May you lead without limits,

They update their résumé, scroll LinkedIn, and set up a few coffee chats — and then wonder why the process feels slow, discouraging, or opaque.

In my first Lead Without Limits LIVE, I sat down with Kristof Shoenaerts, executive headhunter and author of Job Search Unlocked, to talk about what really matters before the job search even begins.

Kristof leads the global life-sciences practice at a top-ten executive-search firm and has placed hundreds of senior leaders worldwide.

Here’s what we learned.

Read more

Join me today for a free Substack LIVE on the 5 Things Every Leader Should Do Before They Start their Job Search with Kristof Shoenaerts of Job Search Unlocked — 10/21 at 10:30 am ET (link to join).

Funny how the same leader who can make a million-dollar call in 10 minutes…
can spend years stuck in “Should I quit my job?” limbo.

“Should I?”
“Shouldn’t I?”

Followed by “What if’s” and “I’m not sure’s.”

I hear this from successful leaders every month.
Their past achievements are no match for the fear and doubt they feel.

The whisper of an idea of what they might want going forward — a quieter life, a different job, a new location — gets brushed aside by a more powerful force: fear.

Even if they have figured out how to manage it in many situations, fear can still hold them back..

Your career is an incredibly meaningful part of your life.
Don’t let fear dictate what you do next.

What led to my first big career change.

I know what it feels like to feel scared about making a change.

I made my first series of career decisions completely based on scarcity, status, and other people’s opinions:

• Study finance because it was the most prestigious at my school

• Go into investment banking because it’s the hardest job to get

• Climb the finance pyramid because that’s how you’ll know you’ve arrived

Little of this was based on my talents, my interests, or what actually mattered most to me.

As a result, I worked myself to the ground, got incredibly ill, and left my investment banking analyst program 3 months shy of completing my 2 year commitment.

I didn’t get an offer from one of the coveted private equity or venture capital firms. I didn’t get promoted to Associate at my bank. I didn’t join a hedge fund.

After 4 years of intensive study, a highly competitive job search, and almost 2 years of 100 hour work weeks, I left the entire Finance industry.

I had supposedly arrived on the mountain that would take me to the pinnacle of success. It was for some people.
But not me.

It wasn’t a bad place filled with bad people. It wasn’t a bad job.
It just wasn’t the right situation for me.

In some ways, I was very unlucky: I had made a career choice that led to me getting so ill, it took me years to regain my health.

In other ways, I was very lucky: I learned within 2 years of graduating college that if I was going to have a great career, it was not going to be on any pre-determined track that someone else was going outline for me.

I was going to have to map out my career by taking risks and make moves.

Why we struggle with career change.

We think it’s about money or status.
But it’s really about uncertainty.

Evolutionarily, our brains are wired to seek out predictable outcomes. We can’t make plans when we don’t know what will happen next.

And when you’re considering a career change, uncertainty is the dish du jour.
Your brain is programmed to reject that risk.

High achievers are used to being at the top of the food chain — they are used to being the winners, predictably.

When you make a change, all of that goes up in the air.

Even for me as a relatively recent graduate, it was hard to put all of my past decisions into question by shifting direction.

It’s scary to switch up the context, the rules, the people, and the skills necessary to win. In fact, you might not even fully understand the new game for some time.

The risk of failure is how we translate uncertainty. The brain can’t handle the unknown, so we immediately imagine to the worst outcome: disaster.

Exposing yourself to the risk of losing feels nonsensical. I get it.

And yet, if you let your fear of uncertainty dictate your career, you will not only miss out on tremendous opportunities, you will sabotage your future.

Don’t wait too long to make a shift.

It may seem easiest to stick with what you know. But if what you know is no longer satisfying you, staying on that path is the surest way to burnout and failure.

I knew in my internship that investment banking wasn’t for me.
But I was too scared to risk trying for another job.
So I kept going… straight into burnout.

It was a heavy price to pay for being scared of making a change.

You can’t do well in something that doesn’t engage or energize you. It might not happen immediately, but eventually it will.

You need to pause and step back:

Your job isn’t the problem.
Your inability to leave it and find a new path is.

Career risks are valuable at any stage.

The good news is that making a change can be helpful and effective throughout your career:

Early in your journey

You have fewer stakes the ground, little to no existing reputation, and a much to learn.

Why Take a Risk? It can be a great way to expose yourself to new industries, people, and skills. What you learn will inform the rest of your career.

—

Midway through your career

You might have more responsibilities, and financial obligations. Your existing wins might feel more precious, and your network may feel more entrenched in one area of another.

Why Take a Risk? Broadening your choices could be exactly what you need to maintain optionality and growth into the next phase of your career.

—

Later in your career

You have a proven track record, accolades, and milestones you’ve earned. You have fans across your various roles.

Why Take a Risk? You’ve established your reputation and are respected by many. You have nothing left to prove and you might have fewer obligations at this point in your life. Now’s a great time to try something just for you.

—

The moment you make a change matters less than the type of change you are seeking and why.

The different types of career change to consider.

Because we are wired to seek security and reduce risk, some of us aren’t even sure what types of career opportunities exist because we’ve worn blinders for so long.

Career change can take many forms:

• Changing industries

• Transitioning functions or departments

• Adjusting your role and responsibilities

• Going from people manager to individual contributor

• Changing from a salaried position to freelance, consultant, fractional leader and/or self-employed

• Shifting from doing one job to having a portfolio of roles and income streams

• Transitioning from employee to owner (or investor)

Your career decision impacts your:

• Compensation & benefits, including amount, predictability,

• Your day-to-day schedule

• The people you work with

• What you need to learn

• The skills you use

• Your location

If you’re not sure what you long for, that’s normal.

Use the lists above as a guide. Explore each of the items — the changes and the impact areas.

Talk with your partner, a close friend, a family member to help you determine what matters most to you. It’s OK if it’s only one thing, and it’s OK if it is multiple.

Use what you discover to help you clarify the change you want.

How to reduce the risk.

Once you have a sense of what matters to you, don’t be surprised if your fear gets even louder and more demanding. It’s sensing that you are moving forward, and it will want to pull you back.

The loudest message it will send over and over again:
“You can’t. You shouldn’t. It’s not safe.”

The best way to calm your fear is to reduce the risk.
Here are some practical ways:

• Give yourself financial wiggle room. Save more, reduce your spending. Beef up your emergency fund. When you have a cushion, your fears are easier to quiet.

• Make time for research. Understand the path you want to go on. Learn about the industry, the job, the skills, or whatever is relevant to the shift you want to make. Talking to people is one of the best ways to learn. More conversations = more intel.

• Start a side hustle or project. The best way to learn is to do. Do a trial run in the area you interested in. Nights, weekends, or even on a vacation trip. Don’t make assumptions, get evidence by the work.

• Build out your skills. Beef up transferrable skills or start to invest in learning new ones. It’s a great way to preview what the new job will require and level you up.

• Warm your network now. Don’t just reach out to folks when you need them. Connect with them now and offer your support. That way, if you need them in the future, it’ll be less transactional.

You don’t have to invest in all of the actions above. Choose one and get started. Even that will reduce your risk, quiet your fear, and help you build momentum.

I’m ready. Now what?

Amazing! If you’re ready to start to make the shift, here are my top recommendations to help you find the right next role and set yourself up for success:

• Network. Your relationships are the best way to get connected to the opportunities that fit your vision.

• Look for places that are in need. When folks are in need, they are more willing to take a bet on someone.

• Be willing to be humble and flexible (compensation, level, title, scope). It’s OK to start smaller. In fact, that is a great way to help you build confidence and grow. Most of the career changes I made came with a set back on salary or title only to be followed by accelerated growth not long after.

• Do the work. The rewards will come if this is the right fit. Being patient is one of the most important parts of making a change. The learning curve can take time, but it will eventually bear fruit.

• If it really doesn’t feel right, it’s OK to change again. But don’t rush to a conclusion too quickly.

• Ask for help. Be willing to no longer be the expert in the room. Ask for support from new colleagues, take a course, or even get a coach.

The path may take time to traverse, but that journey can give you renewed energy and excitement.

Parting thoughts.

If you feel a quiet voice or even a louder one telling you that there is another path waiting for you, you’re not alone.

50-60% of American workers want a different career.
Source: Fast Company

Career changes can come in all shapes and sizes. The question isn’t whether they exist, the question is whether you are ready for them.

Regardless of where you are in your career, if you don’t take risks, you won’t be maximize your opportunities: to grow, to earn, to connect, to impact and to create a fulfilling path.

The best part about career change: they are always available, if you’re willing to search for them.

The key is to stop letting your fear “keep you safe.”

Your future self is waiting for you to take the reins and find the path that’s right for you.

Share this post with someone in your life who needs a nudge to go and seek out what’s waiting for them.

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If this piece resonated with you, please give it a ❤️ to help me reach more leaders who need to push past their fear and change their career path.

And if you’ve been forwarded this post, and it resonated, you can subscribe so you don’t miss my future posts:

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Exciting news! I’ve just opened up 3 spots for the end of the year for 1:1 coaching with me. Book a free 15 min consultation if you want to learn more.

May you lead without limits,

P.S. Join me today for a free Substack LIVE on the 5 Things Every Leader Should Do Before They Start their Job Search with Kristof Shoenaerts of Job Search Unlocked — 10/21 at 10:30 am ET (link to join). You won’t want to miss this!

Layoffs suck. But there’s one thing senior leaders forget to do… and it’s the key to getting back in the game.

“I have tough news. Unfortunately, your role has been eliminated.”

You’d think it would be easier for me to hear it, given how much I’ve said those exact words and scripted them for other leaders.

But no.

Last year, when I was laid off, I was devastated.
Even though I didn’t want the role anymore.
Even though I saw the writing on the wall.
Even though I had a vision of what was next.

It still hurt.

Since then, I’ve coached several leaders through the aftermath of a layoff.
Some called me the day it happened. Others were already coaching with me when it happened.

It didn’t matter when; every time, for every person, it was a gut punch.

Here’s how I help my clients navigate this challenging moment and come out on the other side, stronger.

Let your emotions flow. They are there for a reason.

My first recommendation is always to pause and give yourself a chance to breathe and feel all the feelings. When we are wrapped up tight in our feelings, it’s hard to make strategic decisions.

The narrative and emotions of a layoff are hard:

• I thought I was valued and essential.

• What did I do wrong?

• Who was against me?

• I was so loyal and delivered so much. And this is how they treat me?

• What will my team think? Will they see me as a failure?

• I feel terrible and totally drained.

• What will I say when people ask me what happened?

As a more senior leader, this can be even harder:

• I wanted to make a shift, but I don’t know if I can.

• Will people think I’m too old to take on big roles?

• Will I make the money I used to make?

• What if my best days are behind me?

• Is this the end of my career?

While I don’t recommend dwelling on the stories you have and your emotions, it’s important to acknowledge them.

Here’s how to let the emotions flow through you:

1. Move your body.

Go for a walk. Cry ugly tears. Punch a pillow.
Don’t bottle that stuff up — it’s poison.

2. Compassion is the key.

Be kind to yourself.
Acknowledge the grief, anger, or fear that you feel. It’s a sign that your job mattered to you. That’s a healthy thing.
When we embrace ourselves, we can let go more easily.

3. Schedule activities and time with people who give you joy.

Whether it’s a best friend, a cup of tea, a favorite movie or song, or a hobby, feeling joy is one of the best ways to heal and re-energize yourself. It’s not indulgent. It’s essential.

4. Strengthen your mindset.

Take a mindfulness course, Positive Intelligence

5. Don’t worry if your negative emotions re-emerge.

They did for me — often when I woke up in the middle of the night, I was bombarded by a swirl of thoughts. This happened for 4 months. When they come back, just let them be. Don’t judge yourself for having them. They will pass.

Over time, your negative thoughts and feelings will fade. It’s counterintuitive, but the space you give them to flow through you will help them pass faster.

After you’ve given your body, mind, and heart time to process, now you’re ready for more strategic decisions.

One step at a time: Finish leaving before you start seeking.

After you’ve given yourself a bit of time with your emotions, it’s time to deal with the practicalities of the layoff:

• Negotiate your agreement: Severance, healthcare coverage, support services, references, and anything else you need. An attorney isn’t essential, but they can be super helpful.

• Gather contacts & information you need: Most companies don’t allow you to take proprietary information, but there might be elements of your work that you can take with you. Take a minute to figure out what that is.

• Summarize your wins & accomplishments: Jot down these details and make a copy of your performance reviews so that you can reference them later.

• Get a handle on your financial situation (with your partner): Assess how urgent it is for you to find a new job. Reduce expenses if money is a concern. A conversation now will save you a lot of headaches later.

The departure process might take you a few hours to a few weeks or even months.

Here’s a secret: Don’t rush yourself (as long as you pay attention to legal deadlines).

It’s normal to feel tremendous pressure to jump into the job search: Update your resume, apply to jobs, and start reaching out to people in your network.

All of those activities matter, but there’s a very simple reason why you should take your time:

How you feel is what you will attract.

If you aren’t feeling confident, optimistic, grounded, your conversations will reflect it.

You don’t have to know exactly what industry, company, or title you want. But you do have to energetically be ready to engage with others about your job search before you start it.

If you’re not ready yet, that’s OK.

The last thing you want to do is dive head first into the process only to alienate contacts or communicate poorly what you want because you didn’t give yourself time to process and decompress.

You don’t have to isolate yourself. Get the support you need: friends, family, a coach, and/or a therapist.

Just don’t make those conversations about finding a job… just yet.

If you’re one of the lucky people with either savings, a partner who is still working, or a significant severance package, don’t create false pressure to move faster.

If you need more time and can afford it, take it.

Consider a longer pause — a sabbatical. I took one last year and it was a time of great rejuvenation and self-discovery.

I gave myself permission to vegetate in front of the television and I invested in my learning and preparation to launch my business. You can do both. You can neither.

You can do whatever the h*ll you want!

That’s the thing that gets lost (and hopefully found) when you lose your job:
You get to decide what’s next.

You’ll know when the time is right to shift into seeker mode.

One morning, you’ll wake up and feel like “today’s the day.”

You might feel a surge of energy, or just the glimmer of hope that there isn’t darkness and dread on the other side of your morning.

When you feel that sense of possibility, now’s the time to get started on your next career adventure.

Here's the simple framework I walk my clients through:

Want + People + Learning = Opportunity.

Here’s how I break it down:

1. Write Down What You Want

Don’t judge what comes up. It might be vague, it might be specific. It doesn’t matter. Just jot down what is true for you. This is what you dream.

2. Clarify Your Non-negotiables

Compensation? Location? Level? Industry? Culture? This is your bare minimum.

3. Connect with People You Trust

You don’t have to perform for them. You can have raw, unfiltered conversations to help you shape your vision and your narrative.

4. Refine Your Vision

After each conversation, capture what you learned and update your wants if they have changed.

5. Update Your Resume & LinkedIn

See these as iterative, living documents that will change over time.
Recruiters are searching for great talent every day. Make sure you can be found. (If you want help, check out )

6. Make a List of Companies & People You Admire

This will become your Wish List. Your job will be to connect with people who are connected and can make an introduction.

7. Reach out to More People

Former coworkers, fellow alumni, people from community groups, and more. Ask for introductions, and broaden your circle.

8. Attend Conferences & One-Off Gatherings

Virtual conversations are great 1:1, but there is nothing like the energy and the possibilities that can come from in-person events.

9. Rinse & Repeat

You’ll keep repeating the steps above until you find your next opportunity.

The best part? This process will works regardless of what are searching for: a corporate job, a business to build, or a consultant or fractional leader.

You can still search for jobs and apply, but the system is rigged against applications.

50-80% of senior level roles never get posted. When companies have a need for senior talent, they tap into existing staff or a leader’s network to fill the post. This is why networking is so essential.

You need to be in the know as the role is being concepted. Not when it’s fully-formed.

Connecting with people will help you make inroads far faster and far earlier in the process than any digital application.

The road may be long, but you will get through it.

The average time to land is now 12-18 months for a senior leader. That’s the average. It could be shorter, but it could also be a lot longer.

Aim for a fast landing, but be ready for a long one.

A healthy mindset is an enormous asset during times of uncertainty. Give yourself an edge by setting the right expectations and not creating false hope.

Be patient, give yourself some love and care, and take it one step at a time. That is how to not just weather the marathon, but enjoy the scenery along the way.

The people you’ll (re)connect with, the organizations and industries you’ll get exposed to, and the self-discovery that emerges will all make you a stronger leader and better prepared for your next chapter.

So if you're wondering how to get back in the game after a layoff…
Start by remembering this:
You don’t need a plan to move forward. You just need momentum.

You’ve got this. And I’ve got your back if you want help.

👥 Know someone who’s been laid off?
Forward this to them. It'll remind them they’re not alone.

📅 Want support?
I’ve opened 3 coaching spots for late fall. Book a 15-minute complimentary Strategy Call.

Thank you for joining me this week.

May you lead without limits,

You’ve achieved everything you were supposed to:
The title. The salary. The team. The results.

But now… you're here.
In the in-between.

Maybe you've left a big role, or you're still in one — but something’s off.
You can't see what’s next. And that terrifies you more than you'd like to admit.

You dug up your resume. You’re tweaking your LinkedIn, adding wins, roles, metrics. But it feels… empty.

Because you’re trying to move forward using the language of your past.

You don’t need a resume rewrite.
You need a story reboot.

“The stories we tell literally make the world. If you want to change the world, you have to change your story.” — Michael Margolis

If you want to change your world, you have to change your story.

You know that storytelling matters.

It helps you lead, persuade, and land your message.

Great stories don’t just paint a picture; they make you feel something, something that stays with you… long after the meeting, the video, or the performance.

But storytelling isn’t just for your next interview, Board meeting, or when you meet someone new.

It's for you.

It's how you see yourself and what you stand for.
It's how you celebrate your wins and your progress.
It's how you keep your values and priorities clear.
It’s how you meet the people who will help.
It's how you attract what you seek.
It's how you deter what you don't.
It's how you stay grounded.

It's how you evolve you.

I didn’t embrace storytelling until I started my coaching practice.

For me, it began as a means to an end.

Yes, I had been storytelling for my entire career, my entire life.

I had done it intentionally but only narrowly, for specific moments, with specific people, for specific ends.

I was focused on packaging myself as a competent executive:
Someone people could trust to lead organizations. My narrative arc was centered on KPIs tracked, skills developed, and goals realized.

My hero’s journey included revenue turnarounds, difficult people dynamics, and new business models.

And it worked. From the back office to the front office. From analyst to CEO. It made me leadership material: proven, desirable, and a safe bet.

But left so much unsaid.

There wasn’t room for all of me.

My health crises, my postponed art journey, and my conflicts about becoming a parent and having an ambitious career—I told myself it wasn’t safe or relevant to include these pieces of me in the past.

My clients, my Boards, my team wouldn’t understand.
It would be worse than distracting. It would undermine my credibility.

Now, on my new path, not as a representative of a company, but as my own brand, I wanted to be fully seen.

I stepped back and built a broader tapestry of both where I’ve been and where I wanted to go next.

This was a chance to reimagine my story.

So I delved into health challenges, mindset breakthroughs, my misses as a leader, and things I’ve learned from my family.
Topics I would have never shared in my corporate life.

Nearly a year later, I’m still reimagining my story, each week as I write this newsletter and my Substack Notes and LinkedIn posts.

Every piece is a chance to convey another nuance, another element of my arc.

Some have become essential parts of my story.
Others remain tangents I no longer need to test.

Every time I share something that I would have never shared in the past is an act of courage. At first, I wondered if I was sharing too much or if my stories mattered.

“Even if it helps just one person, it’ll be worth it,” I tell myself.

Nearly a year later, I can tell you: it’s been worth it.
Not because I helped others—though I did, sometimes..
But because every time I share, I reclaim more of myself.

My multiple facets bind together and make me stronger.

Perhaps I would have been a better leader if I had integrated more of me into my narrative, even in my corporate days.

What if I had given the people around me a chance to see the whole me?

I won’t ever know the answer, and I can’t change the past.
But I know that crafting a holistic narrative this past year has transformed my sense of self and my power.

You can do this, too.

Your story is waiting for you to tell it.

It might be exactly what you need—to make sense of your journey thus far and to carve out where you want to head next.

How to Create Your Story

Find a quiet place where you can be undisturbed for at least 30-45 min.

Use a notebook or a voice note app — you can be sitting or walking.

1. Ask yourself:

• What am I proud of?

• What do I crave more of?

• What’s missing in my current narrative?

2. Go deeper:

• What gives you joy

• What makes you sparkle

• Who is someone who inspires you

• What drives you forward

3. And when you're feeling courageous:

• What part of me have I edited out for the sake of being “professional”?

• What story am I avoiding — but secretly want to tell?

You don’t have to start sharing this.
You just have to start seeing it.

Because until you own your story, it will own you.

A Final Invitation

If you’re in the midst of a transition, you don’t need to have the answers.

But you do need a story that lets you ask better questions.

Start writing.
Start remembering.
Start reclaiming the parts of you that you’ve tucked away for too long.

Not for your LinkedIn.
Not for your next role.

For you.

Your Turn

What parts of your story are you still figuring out?
Share below — someone else might be walking that same path.

If this post helped you, tap the ❤️ and pass it along to someone else who needs to reimagine where they’re headed.

And if you’re exploring your next chapter — I’ve 3 asynchronous coaching spots open for this fall.
Message me or book a 15-min chat to see if it’s the right fit.

Here’s to leading — and living — without limits,

Special announcement for my subscribers:
I’m piloting a new coaching model this fall — unlimited asynchronous coaching (yup, really). Only 5 slots.
DM me or book a 15-min strategy session to learn more.

Linda was a successful pharmaceutical exec. Three promotions in six years. That’s rare. Very rare.

On paper, it looked like she just picked the right department at the right time.

But if you knew the inside story, you’d know it wasn’t just the company. It was her boss — Brad, the CMO.

Brad was a wunderkind.

He graduated with honors. MBA at 19.

Climbed the ladder in a major tech company. Got poached by a CPG giant. Launched several brands. Then pharma came calling.

Brad was a unicorn — a visionary who could execute.
Built strong teams. Attracted top talent. Gave clear marching orders — then total freedom.
Feedback? Brutally direct. But fair. And kind.

When one employee had to care for a sick parent, Brad didn’t blink — flexible schedule for months so they could keep working and be there for family.

Linda frankly got lucky working for Brad.

She earned the role, no question. But she barely knew Brad when she started. She researched the company. The products. The strategy. But not the boss.

Over six years, she appreciated Brad’s style — but didn’t realize how much she was absorbing from his leadership. She didn’t see how often he was modeling leadership — right in front of her. She didn’t know that when she stumbled, he could have stepped in — but didn’t. He let her figure it out.

Linda also didn’t realize the pace of her promotions wasn’t normal. Brad had been pulling strings — in the best way.

Sadly, she learned the hard way — a few years later. She took a bigger title at another pharma company…

And her new boss? The polar opposite. Toxic. Distrusting. He nitpicked every win, ignored her ideas, and made her dread 9am.

Five years. Zero promotions. Bad habits creeping in. Confidence shot. Burnout brewing.

Linda could still change course. But five years of stagnation? That’s a steep price to pay for not vetting your boss.

Finding a great boss is the most important part of finding a great job.

It may seem surprising that your boss matters more than the industry or function you choose.

But the reason is simple: the best bosses are strategic about the organizations they choose to join.

They maximize the opportunities to win, and you will benefit from their wisdom and their due diligence.

They won’t always get it right, but they will always try to do right by you so your risk is lower even if they make a mistake.

1. Know what you’re looking for great boss.

Many qualities can make for a wonderful person to lead you, but these are some of the most essential:

• Excellent at setting goals

• Delegates and prioritizes well

• Recognizes and rewards their team’s work

• Committed to their team’s growth and success

• Has a track record of people growing in their team and beyond

• Manages up well and secures the resources their team needs to win

• Communicates directly and doesn’t shy away from tough conversations

• Attracts and hires people who complement them and their teammates

• Possesses these traits: focused, ambitious, kind, curious, accountable

For more senior leaders, they are first and foremost excellent strategists: able to read the tea leaves, anticipate customer and market shifts, and understand people and power dynamics so that they can position themselves and their teams well.

These people are rarely caught off guard, distracted, or fall behind. When you work with a leader like this, they will create the tailwinds that will help you advance.

2. Due diligence your boss, just like they background check you.

When you get the offer, and possibly before, if you feel bold, you want to understand:

• What is their vision for their career? What do they aspire to? Why?

• Their career trajectory:

  • Did they jump around a lot? Did they stay and get promotions?

  • What types of roles have they held - are these areas of interest for you?

• Who have they learned from? Who has been their mentor?

• How do they think about performance:

  • What factors matter most to them?

  • How do they handle underperformance?

  • How do they handle high performers?

  • How do they give feedback? Are their people ever surprised?

  • What’s the promotion history of their current team?

Just as your hiring manager is doing reference checks on you, you should be doing reference checks on your potential new manager

• Check for LinkedIn recommendations or comments on their posts.

• Find common connections and ask for other mutual connections.

• Ask to talk to their other direct reports.

• Connect with alumni of their department.

Here are some of helpful questions to ask:

• How do they handle conflict? With themselves, within the team, with other departments?

• How do they give feedback? Do they address it early? Are they clear? Do they give you space to process and respond?

• Do they gravitate towards team members with certain characteristics: e.g. great communication skills, ability to navigate numbers, or more introverted?

• What is their track record of performance within the organization?

• What is their track record of developing leaders? Where do people who report to them go on to do?

3. Don’t give up if they don’t make a great first impression.

If you get to the company and find out your boss is not as strong as you thought, start to look around for other strong leaders.

Before you do — try to do a double check

• See if your boss is open to feedback. Test the waters with something as simple as “Would you be open to talking about how we work together?” Use that conversation as a chance to dive deeper into what they’re looking for in a direct report and what you’re looking for in a boss.

• Talk to other direct reports.

• Talk to other leaders who are peers of your boss — handle these carefully, but they can be the source of excellent intel.

Interviews are notoriously bad ways to get the intel you need, but once you’re on the job, it’s hard to hide the truth.

If you’re not seeing indications that they are open to talking or improving or if you’re finding new evidence points that they aren’t going to be a good boss, then it’s OK to move on.

Pivoting is not a sign that you failed. It’s a sign that you are willing to learn and adapt.

4. Build a pipeline of potential great bosses by developing your network.

For those of you who know me, you’ll know that I believe it’s always a good time to network.

In fact, when you’re happily ensconced in a job you like, that’s the exact moment you should be finding a pathway to your next role.

It’s far better to connect with people when you are happy, fulfilled, and excited about your day-to-day than when you are feeling down.

I’m not saying you can’t have fantastic conversations when you are unhappy, but it will require more emotional labor, and you might find it hard to build momentum.

Always be on the lookout for great boss potential. Some great ways to do this:

• Talk to your friends. If they have a great boss or hear of one in their organization, ask for an introduction or try to find a common connection

• Read and follow thought leaders. Social media and press are great ways to find leaders who are being lauded for their results and their approach. There is a bit of marketing here, but by and large, the jerks aren’t the ones being acknowledged, and even if they are, a little digging around them will surface that take.

• Join memberships and associations. Your alumni network, industry associations, or other membership groups will often have speaker events, networking sessions and conferences, which can be a great way to get exposed to people who you might want to seek out as a boss in the future.

5. Have a great boss? It’s time to cultivate your relationship.

You chose them for their values and their track record. But you might not know how they work and what really makes them tick.

You also haven’t been in the trenches with them, and until you do, you won’t know how your joint chemistry will react to surprises, setbacks, and stresses.

You have an opportunity to start not just on the right foot, but in a thoughtful manner, where you are building trust up-front by talking about the hard subjects before they become awkward.

Similar to my post about The 10 Uncomfortable Topics You Should Discuss with Every New Employee and about writing your Operating Manual, consider initiating a conversation or series of conversations with your boss to discuss some of these topics.

Here’s a simple message template you could use to set it up:

Hi [boss’s name],

I’m so excited to be part of the team. We had some great discussions in our interview process [and as part of onboarding], and if you’re up for it, I’d love to dive a bit deeper with you.

I’ve found that the most productive working relationships are built not just through the work but by aligning on key principles and talking about gnarly subjects like:

• What is your vision for success for yourself, your team, the company?

• When has someone missed the mark? What do you wish they did differently? How did you address it with them?

• What keeps you up at night about my role or function?

• What keeps you up at night about the company’s goals or progress?

• If I were to really knock it out of the park, what would that look like?

• If I have feedback for you, how would you like it shared?

• If I or someone on my team disagrees with you or someone else on our leadership team, how have you seen it handled well? Poorly?

We don’t have to go over all of these at once, but I wanted to introduce the idea of aligning on these so that we know in advance how we can best navigate difficult situations in the future.

Happy to set up time at your convenience!

The idea isn’t to boil the ocean. But you also don’t want to avoid the topics that feel the highest risk.

The best time to dive into the hard stuff is at the beginning of the working relationship, when the slate is clean and when neither of you has baggage with each other.

Jump on the opportunity to get into the hard stuff early.

6. Don’t be afraid to move on from a great boss to find another one.

Staying with a great boss is very appealing, but their career goals may not align with yours. Sometimes, it’s as simple as capping your ability to grow because they exist — structurally. This happens when they occupy the only seat above your seat.

But sometimes it’s more nuanced.

Perhaps they are nearing retirement and losing steam whereas you are ramping up or at least wanting to maintain your trajectory.

Another example is if they are fully entrenched in a function or industry while you want to change to another.

Or perhaps they are focused on an area where you don’t have expertise or interest. They are being a great boss, respectful, present, but they aren’t focused on your functional area. They are focused on another area of the business because that’s what the business strategy requires.

This isn’t an us vs. them issue. This is a signal for you to assess if you should move on and find a role or an organization where you are the focus.

Instead of staying the course simply because you love your boss, you should consider moving on. If they are as wonderful as you believe them to be, they will be supportive of your decision and this will be an opportunity to plan the move with their help.

Key Takeaways

Finding a great boss is one of the most important and effective ways to accelerate your career.

Here are some steps to help you find the right ones for your journey:

• Understand what makes for a great boss. Define the attributes clearly.

• Gather intel about any potential new bosses during your interview process just as your new boss will gather intel about you

• Use your onboarding process to dig more deeply into how your new boss operates and makes decisions. This is an excellent time to navigate tough subjects because it should feel less risky.

• Leave a boss where you are seeing warning signals or signs that they aren’t willing to improve

• Don’t be afraid to move on from a great boss if your goals or focus areas no longer align.

Because in the end, who you work for will shape who you become. If you’re making a career move this year, choose the person — not the job. Your future you will thank you.

I’d love to learn from you: What are some of the key ways a great boss has helped your career?

Want more from me?

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Thank you for joining me, and I look forward to seeing you next week!

May you lead without limits,

P.S.

I’m piloting a new coaching model this fall — unlimited asynchronous coaching (yup, really). Only 5 slots for leaders who want a more flexible coaching model.

DM me or book a 15-min strategy session to learn more.

“I’m tired of answering to a boss... but I’m not an entrepreneur.”

My client, David, a successful global technology business leader, dreamed of a different life, one where he called the shots and didn’t have to globetrot every few weeks across 5-10 time zones and leave his family behind.

David’s company isn’t in distress, his job isn’t threatened. But his soul?
Yeah... that was quietly cracking.

So he called me before it got bad.

He could see it coming.
That awful feeling of “trapped” that sneaks up on high performers when the ladder gets shorter the higher you climb.

His wife wants him to stay on the safe path, the corporate one, where status, salaries and benefits felt predictable, secure.

But David...
He started hearing that whisper:

“What if you controlled your schedule? What if you were the boss?”

Problem was, he didn’t want to build something from scratch.
No crazy idea. No cofounder. No pitch deck.
He wasn’t an entrepreneur.

But I told him...

There’s a path most execs never consider — even though it’s quietly minted thousands of millionaires.

The hidden shortcut? Buying a boring business.

Let me introduce you to the most unsexy secret to building wealth that Wall Street doesn't want to talk about...

Main Street Business Ownership — aka, the secret playbook Codie Sanchez wrote about in Main Street Millionaire.

I found Codie in 2024, just as I was questioning my own next chapter.
And yeah, it totally short-circuited my brain.

Why?

Because it made boring businesses sexy again.

Here’s the simple formula:

Positive CashFlow + Seller Financing + Operational Rigor

= Wealth

It’s not magic. It’s just... practical.

Unlike startups, Main Street businesses don’t need to lose money for 5 years.
They have to make money or they die.
So the businesses that survive?

They cash flow. Day one.

And that’s your cheat code.

Wait... you can buy a business with their money?

Yup.

Instead of emptying your savings or begging a bank, you use seller financing.
It’s like buying a house where the owner gives you the mortgage.

They stay involved (to help). You pay them back from profits (not your pocket).

Lower risk. Higher alignment.

Think about it: Why build a shaky startup when you can buy a proven, profitable one?

Millionaire math made simple

Stats time:

• You’re 10x more likely to become a millionaire if you own a business (Thomas Stanley, Georgia State University)

• Most millionaires are small biz owners — not execs, investors, or heirs (WSJ)

• You earn a living from the cash flow… but you build wealth when you sell the business

That last point is key. The real payday comes when you grow and exit.

Just like flipping a house. But instead, you're flipping an income stream.

Let’s get real: This ain’t passive income.

Codie doesn’t sugarcoat it.
This path isn’t “set it and forget it.”

You need to:

• Know your genius zone

• Do the homework (aka vet a LOT of businesses)

• Hire and manage people

• Deal with fires

It’s work. But unlike corporate work... it’s yours.

You sweat now so you can rest later. Especially once you hire an operator and stop being the day-to-day hero.

The real magic of the model is shifting your wealth creation mindset.

Instead of trading your hours for income, you are building value that grows based on the outcomes of strategic decisions and actions, not how much time you spent on those decisions or actions.

Codie’s argument is that ownership is the only way to build true wealth.

So... is this right for you?

Maybe.

David?
He’s a highly operational exec. He lives for systems. For him, this path is a no-brainer.

Me?
I’m focused on coaching and creativity. I like my life lean. I don’t want another org chart right now.

But just knowing this option exists changed how I look at wealth building forever.

Bottom line?

It’s not about which is better... it’s about who you are.

Do you want to be active in creating your wealth...
Or more passive, letting the market do the work?

Both paths have risk.
Just different flavors.

Closing thought: Get curious to avoid getting desperate.

If this post got you excited about business ownership, now is a wonderful time to start to explore. The most successful people get educated early.

Two ways to get smarter on business ownership fast: (1) speak with people who’ve already traversed the path, (2) pick up Codie’s Main Street Millionaire book.

If you’re like me, you’re thoughts on which path you want to pursue will ebb and flow. That’s OK. All the more reason to give yourself time to figure out what will be right for your life.

Don’t wait until you feel pressured. Do it when you have the most optionality.

Your Turn

Have you ever considered business ownership? Are there resources you’d recommend? I’d love to learn from you. Share them in the Comments to help others in the Lead without Limits Community.

If this post helped you, tap the ❤️ and share it with someone who's sick of corporate but not cut out for startups.

Share

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Thank you for joining me this week.

Subscribe, and you can direct message me through the Substack app. I love hearing from readers and respond to every message.

May you lead without limits,

P.S.

I’m testing a new coaching model — unlimited asynchronous coaching (yup, really). I’ve got 5 slots open for fall.

DM me or book a 15-min strategy session if you’re ready to level up.

“I have tough news to share. We’re eliminating your job.”

Ten words no one I’ve coached — or met — is ever fully prepared to hear.

First, your gut clenches. Your heart races. Then comes the storm: a swirl of shock, fear, guilt, and shame.

And just when you need your clearest thinking, panic takes the mic:

“What am I supposed to say?
I thought I could trust them.
How will I tell my family?
Can we still take that vacation?
Should I return the new suit I just bought?
What am I going to do?”

I’ve sat across from hundreds of leaders in this exact moment. I’ve delivered the message to over 300 employees myself. And yet, when it happened to me in early 2024, I still heard that voice inside whisper-screaming:
“Wait… what?!?”

But unlike many, I found myself surprisingly calm — because I was prepared:

• I had a financial cushion. Not for a few months — for a few years.

• I had a plan. I’d known for decades I wanted to coach.

• My partner and I were aligned. There was no blame, just clarity.

I still had to feel the loss. But I didn’t have to feel the fear.

No one can predict the future, but you can prepare for it.

We are living in volatile times: economic uncertainty, global unrest, technological disruption. Even the most high-performing leaders are getting blindsided.

Reskilling and personal branding matter. But you can do all of that right — and still get swept up in change you didn’t choose.

This is why today’s post isn’t about growth.
It’s about freedom.
And that freedom starts with your safety net.

Because true career security isn’t earned at the office.
It’s built at home.

Why most leaders stay stuck.

Nearly every executive I coach has thought about making a major career change. Many, more than once.

But they don’t.

Not because they lack ambition or opportunity.

Because they lack financial security.

They want to move closer to family — but can’t walk away from the paycheck.
They crave a more flexible role — but feel handcuffed by their mortgage.
They dream of building something new — but worry they can’t afford the risk.

It’s a sad, but true fact:
Money won’t make you happy, but the lack of it can keep you stuck.

The two levers of career freedom.

There are only two ways to create financial freedom:

1. Earn more.

2. Spend less.

Do both, and you’re future-proofing your career — and your life.

I didn’t know what “FIRE” (Financial Independence, Retire Early) was until my 40s. But I was already living many of its principles:

• Aggressive saving

• Strategic investing

• Minimal lifestyle inflation

• Conscious trade-offs for long-term freedom

This didn’t mean I stopped working. It meant I worked on my terms.

My motivation for financial independence started early.

As a kid, I dreamed of being an artist. But I knew how hard money was to come by. My immigrant parents couldn’t afford the “extras” — expensive toys, study abroad, and trendy clothes.

So I saved. Worked every summer starting in high school. Opened a Roth IRA and maxed it out as a teenager every year. Applied for every scholarship I could find.

By my mid-20s, I bought my first apartment in Manhattan.

Not because I made millions.
Because I made conscious, consistent decisions.

I wasn’t going to let my dreams be limited by the size of my bank account.

And neither should you.

8 Habits the Created My Safety Net

Note: I’m not a financial advisor — just someone who’s walked this path and wants to help others do the same. Always consult a professional before making any financial decisions.

1. Save more than you spend.

Sounds so simple, and yet approximately 38% of Americans with an annual income of $100,000 or more carry credit card debt (InvestmentNews, August 2023).

If this is you, STOP.

Stop keeping up with the Joneses.

You don’t live with the Joneses. You don’t have to pay their bills, and they don’t have to pay yours. If someone thinks less of you because your house is smaller or your car is more modest, is that someone you really want to call your friend?

Spending because you think someone else will care is one of the worst reasons to kill your financial dreams.

Stop buying more stuff. Less stuff = more freedom.

• Cut back on what you buy (most people only need 80% of what they buy)

• Instead of filling your life with stuff, fill it with nature, reading (from the library), and people who enrich you

Downsize your living.

• Fixed costs are the hardest to adjust. If you’ve already spent the money and committed, investigate what it would take to unwind your decision. Your future self will thank you.

• Cut everything and everywhere: take public transportation or walk; don’t eat out at fancy restaurants or pay for fancy drinks; choose a less trendy gym; stop getting all the wellness extras.

• Unless it generates long-term value (increasing your skills, is resellable, adds to your income, improves your well-being, adds to your experience, strengthens relationships) and you are actively using it, it is on the chopping block.

Until you save way more than you spend, you won’t be able to build a significant enough financial safety net.

What is way more? For most of my career, I saved 50% of my income post-tax, post-401K, post-healthcare contributions, every year.

The more you save now, the less you worry later.

Don’t wait until your income is disrupted for you to scrutinize every expense.

Do it now.

2. Aim for 18 months of emergency funds.

Take a portion of your savings and contribute it to your emergency funds.

Why 18 months? Because the average executive job search is now taking 12-18 months.

These should be liquid, meaning easily accessible so you can use it when you need it most.

3. Invest what you save on a set-it-and-forget-it schedule.

Invest the money you save in ETFs (exchange-traded funds) on a regular schedule and don't touch them until you approach retirement (as recommended by J.L. Collins, the godfather of long-term, low-effort wealth accumulation).

Why on a regular schedule? Most people (like me) are not day traders and are terrible at timing the market. When you have a set schedule for investing (“Dollar Cost Averaging”), you’ll never miss the ups and you won’t get taken down by the downs.

Why not touch them? What if the market crashes? Over time, the market has always grown. The people who win are the people who stay in the market — for years, decades, multiple decades.

If you’re approaching retirement, you might adjust your investments over time to less risky, lower-growth options like bonds. Plan with your financial advisor to get specific.

4. Take the time to understand inflation and taxes.

No one likes inflation or taxes. They both exist for a reason. And neither are going away.

Do your homework and understand how they impact your money.

Ignorance is a strategy, but not a smart one.

5. Align with your partner.

Don’t try to create financial independence alone. Too many couples make the mistake of making one of the two people “the money” person. And then sadly, “the money” gets sick and passes away, or they separate.

The remaining person is now left completely in the dark.

Don’t be the person keeping the other person in the dark. Don’t be the person in the dark.

Take the time to align together, learn together, and build together.

6. You are the company you keep.

Find your people. Be thoughtful about who you choose.

Share books, podcasts, financial advisors, and other materials with each other. One of my favorites: Katie Gatti Tassin — smart, approachable, real.

7. Understand retirement and what you’ll need.

There is an abundance of free retirement calculators. Many banks and investment firms offer them. Use one. Even a rough estimate is better than flying blind.

Don’t know your monthly spend? Start there.

8. Always have a Plan B.

What will you do if your job disappears tomorrow?

For me, it was coaching. For you, it might be consulting, writing, real estate, or acquiring a small business.

You might have multiple ideas. Awesome. Do light reading on them. Know which one would be your first choice.

You don’t need to act on it now.
But you do need to name it and talk with your partner about it.

Final Thoughts: Don’t wait.

You don’t need a course.
You don’t need a new credential.
You don’t need permission.

You just need to start.

Because if your career hits turbulence, your past choices become your parachute.

In Brief

When in doubt, talk to your financial advisor and accountant. These 8 steps can get you started:

1. Save more than you spend.

2. Aim for 18 months of emergency funds.

3. Invest what you save on a set-it-and-forget-it schedule.

4. Take the time to understand inflation and taxes.

5. Align with your partner.

6. You are the company you keep.

7. Understand retirement and what you’ll need.

8. Always have a Plan B.

Prioritize your financial well-being. No one else will.

Your Turn

Are you building your safety net?

• If yes: What’s worked best for you?

• If no: What’s one thing you’ll start doing this week?

💬 I’d love to hear your story — reply in the comments or DM me through the Substack app.

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The offer hit her inbox and for a moment... everything felt right.
Until she did the math on the move her family now had to make.
“This is gonna cost us a fortune,” she sighed.

As the primary breadwinner for her family, Shuli had beaten the odds.

Everyone told her that it would be another 5-8 months before she might land a role. The economy was less than stable and most companies were wary of taking on more costs.

She had been laid off 7 months prior after spending 20+ years at her very first company, a large publicly-traded financial services firm.

Despite having forged a reputation as an innovative leader, committed to learning and delivering great results, Shuli, like many other leaders, was not immune to the large-scale cost-cutting happening all over the corporate world.

Fortunately, Shuli had nurtured her network throughout her career. The same day the news about the layoffs broke, her former boss, Emily, reached out.

Emily was a visionary leader and had left a few years prior to join the C-suite of another large financial services firm. As soon as Emily heard that Shuli was on the market, she immediately called to try to secure her.

As wonderful as it was to hear from Emily, Shuli knew not to assume Emily’s role would come through. Budgets are hard to secure and decisions could change on a dime. So Shuli started her job search while she waited to hear from Emily.

Eventually, after 6 months of navigating internal bureacracy, Emily got the new role approved, and within 3 weeks, the hiring team agreed with Emily: Shuli was the best candidate for the job.

When the offer arrived in her inbox, Shuli sighed in relief. Months of resume tweaking, ghosted interview processes, and sending out inquiries into a void were coming to an end.

But not just yet.

As Shuli started to evaluate the offer, she was taken aback by what she discovered.

Negotiations don’t have to feel like you are entering a battlefield.

The offer was actually very generous. It included an increase in all the relevant areas that mattered to Shuli: in title, level, scope of role, size of team and there was an increase in base compensation as well as bonus and stock.

Shuli’s first impression was the that the offer was more than sufficient, it was very generous.

However, she had been taught over the years, “you always ask for more.”

She wasn’t sure what to ask for yet, so she started to do a little research about the area she would need to move her family to to justify her ask.

This is when she discovered that as generous as Emily had been, the offer would actually put Shuli’s family in a worse off position than her previous job.

Here’s what Shuli realized.

Always start with data and figure out what matters most.

Shuli’s offer was a 30% increase in total compensation than her prior role. In isolation, that felt like a tremendous win.

The largest raise she had ever received in her past roles was 15%. And this increase was off of her highest compensation level, making the increase in dollars more than 3x the largest increase she had ever received amongst her past promotions.

Everything looked great until she considered that her lifestyle costs were about to dramatically change.

The new job required Shuli to move her family to a place where their cost of living was 1.5x higher than their current location. This didn’t just mean they needed to spend more in day-to-day costs, but also meant that their new house was going to be significantly more expensive.

After doing the math, Shuli realized that not only did her compensation need to increase, but it needed to increase a particular way: in base compensation.

Bonus and restricted stock units are wonderful for motivating performance, but they wouldn’t pay her new, much higher monthly bills.

Even more pressing was her need to buy a home in a highly competitive housing market. She wasn’t going to start this job without knowing that her family was coming with her.

The base compensation in the initial offer would mean that she could only put 10% down for an offer. Real estate agents made it clear that wouldn’t put her on on seller’s preferred buyer lists.

To become a more attractive home buyer, Shuli would need more annual cash income to qualify for a better mortgage.

Without an increase in base compensation, it was going to be difficult for Shuli to make the move.

This was supposed to be a moment of celebration. Instead, Shuli felt deflated. Her perfect job was right in front of her, but now it felt completely out of reach.

How was she ever going to get Emily to make such a rich offer even richer?

Negotiations don’t have to be hard if you are clear about what matters.

As someone who used to fear negotiations and nearly failed her college course on the topic, I’ve always been fascinated by the people who can do this well and still maintain positive relationships and generate great outcomes for all.

Over the course of my 25 year career, I have negotiated my fair share of deals and compensation packages. What used to give me fear, over time, became a source of delight and fun.

Treating negotiations as an opportunity to find common ground and joint wins is like solving a complex puzzle. What often gets in the way is our emotions, and in particular, fear:

• Fear of not getting what you want

• Fear of not handling the negotiations well — perhaps misspeaking, or giving too much away

• Fear of hurting your relationship

How Shuli handled her negotiation is a great playbook to follow for any negotiation.

An open and honest conversation is the best way to start a negotiation.

After a good night’s rest, Shuli got up to a bright and sunny Spring morning.

With renewed hope and energy, Shuli recognized that her fear and anxiety weren’t going to get her what she needed.

So after her morning meditation and a cup of strong, black coffee, she got to work.

Shuli organized her research and laid out a plan for how she would speak with Emily.

Once she had her outline ready, she took a deep breath and sent Emily a text, trying to strike the right balance of urgency without panic, “Hi Emily! Thanks for the offer. I have a few questions. Do you have time to talk?”

Emily responded quickly and they got on a call within the hour.

First, Shuli shared how much she appreciated Emily’s offer and how much she wanted to work together. Then she shared that while her goal was to work together, she had to think about her family’s well-being first, which is why she needed to talk with Emily about a revised offer.

Shuli methodically explained her research and why she needed a different base compensation. She shared that while the compensation overall was generous, it simply wouldn’t enable her to provide for her family in the new location.

In addition to cost of living and housing pricing research, Shuli had asked Emily and her HR contact during the interview process about the company’s pay ranges for her level. This helped her understand where her offer landed her in the company’s compensation bands.

Shuli’s offer had her at the middle of her level’s compensation band. This gave her a sense that while Emily’s budget might be capped, Shuli’s compensation had room to rise without triggering concerns that she was out of the band.

After she shared her concerns and needs, Emily offered to go back and see what she could do.

Note: Company compensation bands are usually not a hard and fast rule. They are guidelines that help the organization budget, plan, and maintain some sense of fairness. If you’re not sure about how your company handles them, ask.

Stay focused on what matters most and you’ll find the path forward much less stressful.

Over the next 3 weeks, Emily and Shuli spoke 4 more times. They clarified what mattered most to Shuli and where she was willing to give.

During this time, even though Shuli was felt uncertain about the outcome, she left each conversation feeling good about how she and Emily were navigating the discussions. It reinforced Shuli’s trust in Emily and vice versa.

They were both communicating with high integrity, calmly and thoughtfully. Even if this didn’t work out, they would both leave feeling that they had exemplified their values and showed up as their best versions of themselves. Their interactions only strengthened their respect for each other.

In the end, Emily was able to increase Shuli’s base compensation by reducing her bonus and stock compensation and adding a bit more on top of all of that to help Shuli secure a smooth and positive transition for her family.

Emily was able to make all of these adjustments because of Shuli’s careful research.

Sharing Shuli’s datapoints with her HR team allowed them to collectively come up with a response that felt in line with company policies while securing their top candidate.

For Shuli, the outcome was stellar.

Within a few months, she was able to sell her current home, buy a new home and move her family all before the start of the next school year.

A great negotiation playbook isn’t complex; it’s thoughtful.

What I loved about Shuli’s approach is that even though the stakes were high, she kept her values and her priorities in mind at all times. This allowed her to show up as her best self and created an even stronger relationship with her new boss, Emily.

Shuli took a tough situation and transformed it into an opportunity.

Let’s break down Shuli’s negotiation approach so that you can use it, too.

1. Clarify what matters to you and why. Ideally create a forced-ranked list (1, 2, 3, etc) so that you know the hierarchy of what is more important and what is less important. Shuli knew that her all in compensation package was fine — she just needed more in base compensation. Having that clarity gave her confidence and steadiness.

2. Know your numbers. Understand the implications of any change in the numbers. Historical context, past changes, company policies, all of these will help you provide context. When Shuli shared all of her research, it made it so much easier for Emily to justify making a change.

3. Treat the person not as your adversary, but as your partner. Don’t try to fight the other person. See them as a collaborator and that you both are trying to get to the same outcomes. In Shuli’s case, Emily and Shuli both wanted to work together. That was their joint-win. They were simply navigating a compensation conversation to achieve that joint-win.

4. Be open, be vulnerable. The easiest negotiations to navigate are with people you trust. Even if you haven’t established trust before the negotiation, every interaction is an opportunity to build trust. Being open and even slightly vulnerable will help you build that trust.

5. Be patient; don’t panic. No one wants to collaborate with someone who is on edge. Before each conversation, calm your nerves and remind yourself that getting to a great outcome may take more time than you want and follow a non-linear path. You may not get what you want every time. But you’ll up your odds if you keep a positive mindset and as they say, “keep calm, and carry on.”

6. Keep your values and the relationship in mind. Even when a negotiation doesn’t work out, how you showed up and how you leave the relationship is what will become the legacy of that negotiation. That’s your long-term win even if you didn’t get the short-term win.

Share your best negotiation strategy.

I’d love to hear from you and what resonated in Shuli’s approach or how you handle negotiations and get to the best outcomes. Click through to leave a comment. I read and respond to every one.

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“We’re going to have to do another round,” Gloria shared with some resignation at the weekly executive meeting.

Mirabelle’s insides twisted.

It was the 5th round of layoffs in less than 2 years. She trusted Gloria, her boss and CEO, and their CFO, Jeff. They were thoughtful and thorough leaders. They wouldn’t do this unless it was necessary.

But sh*t — this wasn’t going to do anything to help team morale.

Mirabelle’s husband had been telling her to start a job hunt after the first round, but she just didn’t have the time.

Well, truthfully, she didn’t want to start to search. She wanted to believe that they could turn it around.

But was she simply sticking her head in the proverbial sand and ignoring the obvious signals that it was time to jump ship?

The market was terrible. Her friends, other senior leaders, had been searching for months — some for over a year without success.

When the markets were shaky, wasn’t the best bet to stay put?

What if she joined another company and it also started to struggle, but she would then have no street cred or existing relationships? Wouldn’t that make her more vulnerable?

Mirabelle was the primary breadwinner for the family, and with two young kids under the age of 5, she and her husband, Anthony, had their hands full.

The prospect of job hunting while trying to lead through disruption and caring for a young family, it all felt like too much.

Mirabelle was facing what felt like an impossible decision that many leaders are grappling with: the conundrum of whether to stay or go when the stakes are high, and the rewards are unknown.

Just like any other challenging decision-making process, Mirabelle needed to break apart the problem and review her options with as much evidence and little emotion as possible.

She came to me to help her navigate this moment, and here is what we reviewed.

Sticking around when others are leaving is not always a bad decision.

Before I dive into the signals that indicate it’s time for you to go, there are many reasons to stick around even if a company is struggling, including learning new skills or honing existing ones:

• Turning around an operation that is underperforming

• Shutting down an organization

• Exploring a sale or liquidation process

• Managing a bankruptcy

There is demand for the skills listed above, and having them under your belt may give you more career options in the future.

In addition, being known as someone loyal to the company until the end might buy you brownie points with the Board and investors, who might be more inclined to call upon you in the future

That said, most people want to get out before the doors start to close.

Why?

Because they don’t want to navigate the experiences above and run the risk of having a gap on on their resume. I don’t mean to suggest that these experiences aren’t worthy, nor that a gap on your resume is bad — because I feel quite the opposite.

But from my experience, most leaders want to be on the growth end of the curve and not on the decline side of the business lifecycle. Some combination of fearing the end and wanting to secure their future financial prospects means that most leaders want to leave earlier, not later.

I’m not judging your proclivity — in either direction.

What I do judge (just a little) is if you don’t try to interpret the signals and take action.

Sitting on your hands is also a decision, it just happens to be one of the worst kinds — a passive and possibly unconscious one that often leads to disappointment.

10 Signals that it Might be Time to Go

Not surprisingly, the signals that matter most are a mix of company attributes and your needs. In general, when they no longer align, it’s time to go.

These aren't necessarily indicators that the leadership team is evil or even bad. It could be that the market dynamics are changing so quickly, the business model just isn't set up to withstand the challenges.

But let’s get more specific.

Here is the list I have honed after more than two decades working in 5 different sectors and living through 3 different major market downturns.

1. Consecutive quarters of missing revenue targets without commensurate cost-cutting

So it might feel like cost-cutting is the sign that you should go. It isn’t.

Cost-cutting can be a sign that you should stay. I’ll say that one more time, cost-cutting can be a sign that you should stay.

The issue for many companies is that they don’t operate in a financially prudent enough way. When cash flow starts to slow or decline, they don’t take action fast enough to preserve the cash they have.

Scaling back spend isn’t always the smartest move. Sometimes, you need to invest more to change the direction of the business.

But more often, you need to cut back, especially when the market is uncertain, you’re not sure yet of the solution, or you need more time for your solutions to bear fruit.

If your organization is missing consecutive quarters of revenue, even if cash flow is still healthy in the short-term, it’s likely to get unhealthy soon. Unless you have a tremendous pile of cash and a very patient Board and investors, you should be conservative with your money, and that means cutting back proactively, early enough and large enough to make a difference.

When the CEO and CFO aren’t making the call to conserve cash, I would be concerned about their priorities and decision-making approach, and whether that is creating more risk than is necessary.

TAKING ACTION:

• Understand the company’s cash position and the impact of revenue on cash flows.

• Track company performance and review it monthly.

• If the organization isn cost-cutting, don’t assume why. Ask the CEO and CFO. Make your decision based on their answer and your level of confidence as a result.

2. Rapid shifts in strategy

Agility is considered a positive attribute in most organizations, but there is a difference between being nimble and being untethered.

Testing new ideas and approaches is good, but how you go about it determines whether the organization can be successful. When leaders shift the focus of an entire organization quickly and without some evidence of the likelihood of success, they are risking creating whiplash and lack focus.

This is usually a sign that leadership is struggling to understand the issues and what to do about them.

Flailing is not a strategy. At least not an effective one.

Contrast that with a more structured test and learn approach that is orderly, methodical, and predictable, and you’ll observe the difference between an organization filled with people who are challenged, but energized versus a team that is stressed, overwhelmed, and struggling.

Changing course quickly is not a sign of decline.

Changing course quickly without bringing your team along with clear reasons why and data to back up the approach is a signal that leadership is losing its way.

TAKING ACTION:

• Track if your company is making rapid strategy changes.

• Don’t just look at your department, observe others as well.

• When in doubt, ask other leaders what they are perceiving.

3. Deep misalignment at the top

There will always be some disagreement — you don’t want your executive team to be in a state of blissful alignment all the time. That just signals groupthink.

The best teams comprise people who differ in skillsets and approach. Those differences will naturally lead to conflict which if handled well will be productive and lead to better decisions.

Deep misalignment is not productive conflict.

Deep misalignment is when different members of the leadership team are at odds with each other on a fundamental level: the strategy of the company, financial management, culture, and interpretation of market dynamics and their response.

The depth of the misalignments refers to how strongly held these differences are and whether leaders can come to a level of agreement that allows them to collaborate and execute effectively together.

The decision makers here also include investors and the Board. They are the ultimate fiduciary stakeholders for the company, and if they are not aligned with management, there will be negative consequences.

When there is misalignment at the top that is destructive, leaders are distracted, stressed, and ill-equipped to focus on the business day-to-day because they are unresolved at a strategic level.

TAKING ACTION:

• If you’re on the executive team, pause to reflect every month or few weeks about how well-aligned you and your leaders are.

• If you aren’t on the executive team, observe what is shared at town halls by each executive leader. Do you hear dissonance?

• When you are not clear about the rationale for a change in direction, ask for clarification. Use information to inform your interpretation.

4. High and rapid executive turnover

As someone who has hired and participated in the hiring process of more than a dozen executives, I can tell you firsthand that the failure rate (~40%) is high for a reason.

Hiring successfully is difficult at any level. There is only so much you can discern from a resume, and during the interview process. The candidate and the company are usually not showing all of their cards, and in hybrid and remote work environments, it takes even longer to suss out how it’s all going to turn out.

Executive hiring is even more challenging, even if the stakes are higher and the process more thorough (or belabored). And if the failure rate is already so high, how much higher can it get. It can be worse — trust me.

High and rapid executive turnover is a sign of misalignment at the top (see above) and an early indicator of turmoil that will trickle down. Teams are resilient, but when there are multiple leadership changes in rapid succession, it’s harder to build trust, maintain a consistent strategy, and keep up morale.

TAKING ACTION:

• Executive turnover isn’t something you might normally pay much attention to, now you want to. Just keep a log of when roles are open, when folks are hired and when folks leave.

• If you start to see a pattern that is increasing in rate, it’s a good time to take a deeper look.

5. More than 3 rounds of layoffs

Why wait for 3? Isn't 1 enough?

As I pointed out in the first signal, you want your organization to make cost cuts if your revenue and cash flow can’t support your current operating model. So 1 layoff round isn’t actually a bad sign.

To be honest, 3 rounds isn’t necessarily bad either. But it could be an indication that your leadership team isn’t doing a great job of anticipating its future performance.

It could be because of truly unforeseen circumstances (e.g. the pandemic), or it could be because there are underlying weaknesses to the business that are not being addressed (e.g. poor product-market fit, strengthening competition, sales issues, etc.) It’s also possible that the leadership team is not cutting enough in each round.

Regardless of why more layoffs are necessary, the signal here is that continued cost-cutting is necessary, which is a sign of underlying business risk that may be a reason to find your exit.

TAKING ACTION:

• Track the layoffs your company does: how many people, rationale, frequency.

• If you don’t feel bought in on why, ask questions.

• If you anticipate another round being necessary, ask early.

  • If you’re interested in existing, consider negotiating for a spot.

  • If you want to stick around, ask more questions to see if this round can be deeper so as to avoid another round in the future.

6. Deteriorating culture

It’s not surprising that people are more agitated and on edge in a declining business. It becomes an issue when this is the default attitude people are bringing to work.

Everyone is allowed a bad day or a bad interaction from time to time. When it becomes a pattern and it starts to feel pervasive across the organization, that’s a signal that the wheels are coming off.

When it’s a one-off, people assume the best intent and can forgive easily. When it is a regular occurrence, people start to assume the worst and may even retaliate, further perpetuating a negative culture.

Culture is not a bunch of catch phrases. It’s the behaviors you practice and live by every day. The entire staff is responsible for the culture that your organization abides by, but the leadership sets the tone and leads the way.

TAKING ACTION:

• Take the time to observe how people are showing up in meetings.

• Ask your team how they are doing and check in on their interactions with other teams.

• The most challenging part of seeing a deteriorating culture is if you are part of the deterioration. So try your best to evaluate when you are not feeling down or depleted.

7. You are no longer set up for success

Cost-cutting may be necessary and a responsible act, but there are times when your budget and staff have been cut so much that you no longer feel equipped to reach your goals.

In addition, when a business is struggling, departmental goals, including yours, may have been increased or accelerated.

The combination of reduced resourcing and harder goals may be OK, unless you don’t think you can deliver. If there isn’t any room to adjust, then it might be a signal for you to take a bow.

TAKING ACTION:

• Assess your goals and what you think is possible with the resourcing you have.

• Discuss this with your boss and relevant colleagues. Understand the implications of keeping (and missing) and changing your goals and what resourcing you might need to hit them.

• Determine if the changes are worthwhile and likely to happen, and if you are open to sticking around to see them through.

• If the changes aren’t something you and other leaders can agree to, decide if you want to stay on and try to hit the higher goals with less support.

8. Your function is no longer essential

Related to not being set up for success is whether your function is still essential to the business. Sometimes, when your function is being reduced significantly, it’s a sign that it no longer matters as much as it did.

This isn’t necessarily an indictment on you or your leadership. It is likely more connected to the overall shrinking or shifting of the business.

But it warrants a hard look.

If you or your function are no longer necessary, then you are, by default, a drain on the company’s cash. The question isn’t whether you will be exited, the question is when. You can either wait for it or proactively bring it on.

TAKING ACTION:

• Do an assessment of whether your function is still essential and whether it should stand alone with an independent leader.

  • You can conduct your own review based on your understanding of the current operating needs of the organization.

  • Consider also talking with your colleagues and your boss. That might be showing your cards, but generally, the risks are low because all you are doing is uncovering what people are already thinking.

• If you find that it still needs to exist, then consider holding your course.

• If you find that it no longer should exist, consider exiting sooner.

9. You don’t believe in one or more of the leaders

When you are part of the leadership team, they are, as Patrick Lencioni wrote in the The Five Dysfunctions of a Team says, your first team.

These are the people you march into battle with daily, shoulder to shoulder, working towards the same ends.

If you don’t think one or more members of the team can do their job successfully, then you’re betting on a weak links.

I’m not talking about someone having a bad day or missing a one-off target. I’m talking about you no longer thinking that they are the right person for their job.

Unless you perceive they will be exiting soon, then your decision to stay on means that you are OK with a member of the leadership (and the function that they lead) not delivering on their responsibilities or targets.

TAKING ACTION:

• Be wary of your read on another leader’s job unless you understand how their function drives the company's success overall and where their weaknesses might create risk.

• If you truly feel concern about their ability to lead and deliver, consider talking with your boss, the CEO first, or to a trusted confidante. Be careful of gossip, you don’t want to spread your judgment widely. You want to seek out additional inputs to try to prove or disprove your take.

10. Your career goals are being significantly delayed or sidetracked

This one might be super obvious. When a job is no longer meeting your needs, it’s time to go, right?

Yes and no.

The reality is that even if your career goals are less likely to be met, your decision to leave depends on the market economy and your priorities.

When the economy is shaky, more companies are likely to be unsteady as well. Your career might be delayed or sidetracked regardless of the place you go.

In 2001 and in 2008, many people’s careers were slowed. Sure there were companies that grew in that period as well, and people ascended, but those were rare.

In addition, there are times when your career will take a backseat to other priorities — family, health, or other personal needs. That’s OK.

In fact, you should expect that the pace of your career growth will ebb and flow. No one’s career looks like a straight line up and to the right.

TAKING ACTION:

If growing your career is your top priority, then a review of the following questions will help you decide your next move:

• Does the pace of your growth at your current company match your vision?

  • Are there enough senior posts that will be available for you to compete for?

  • Do you have sufficient sponsorship (support) from key decision-makers or influencers to advocate for you?

  • Have you planted the seeds of your desire to grow?

• Are you continuing to develop new skills and hone existing ones?

• Is your current role setting you up well for your next opportunity?

Only your interpretation of your organization’s signals matters

After talking through these options, Mirabelle realized that her best path forward, despite pressure from her husband was to stay the course and not leave.

Although the company was experiencing declines, the path to recovery and a return to growth was fairly well-understood. In addition, her role and her function were critical to the company’s future success. Last but not least, she believed in her fellow leadership team members and continued to feel motivated to stay on.

It wasn’t all sunshine and roses, though. She used the list above to prompt her to dig deeper into whether cost-cutting measures were adequate and to be more cognizant about how she and other leaders were showing up at work. Even if the pressure was high, she didn’t want to convey unnecessary or unproductive stress to her team.

Had Mirabelle concluded that she needed to leave, my recommendation would have been to consider the following options.

1. Proactively find a new job and exit

2. Wait for the next round of layoffs and negotiate a package

If you have decided it’s time to move on, it’s time to start reaching out to your network, searching the job boards, and applying to roles. Some resources below to help you consider your next steps:

• “The Most Successful Leaders Do This Before Starting A Search for Their Next Job” — I share more about some reflections you might want to invest in before you go.

• “The Single Most Important Way to Boost Your Career is to Build Your Network” — Some of my top networking tips to get you started.

• “Make a Plan to Break Free from Your Golden Handcuffs Before It's Too Late” — Highlights how you prioritize your non-negotiables before you start your search.

Key Takeaways

Below is a summary of all 10 signals and the actions I recommend above. Would love to know if these resonate with you in the Comments section.

Feel free to share them with friends or colleagues who you think could benefit.

1. Consecutive quarters of missing revenue targets without commensurate cost-cutting

   1. Understand the company’s cash position and the impact of revenue on cash flows.

   2. Track company performance and review it monthly.

   3. If you aren’t cost-cutting, don’t assume why not. Ask the CEO and CFO. Make your decision based on their answer and your level of confidence as a result.

2. Rapid shifts in strategy

   1. Track if your company is making rapid strategy changes.

      Don’t just look at your department, observe others as well.

      When in doubt, ask other leaders what they are perceiving.

3. Deep misalignment at the top

   1. If you’re on the executive team, pause to reflect every month or few weeks about how well-aligned you and your leaders are.

   2. If you aren’t on the executive team, observe what is shared at town halls by each executive leader. Do you hear dissonance?

   3. When you are not clear about the rationale for a change in direction, ask for clarification. Use information to inform your interpretation.

4. High and rapid executive turnover

   1. Executive turnover isn’t something you might normally pay much attention to, now you want to. Just keep a log of when roles are open, when folks are hired and when folks leave.

   2. If you start to see a pattern that is increasing in rate, it’s a good time to take a deeper look.

5. More than 3 rounds of layoffs

   1. Track the layoffs your company does: how many people, rationale, frequency.

   2. If you don’t feel bought in on why, ask questions.

   3. If you anticipate another round being necessary, ask early.

      • If you’re interested in existing, consider negotiating for a spot.

      • If you want to stick around, ask more questions to see if this round can be deeper so as to avoid another round in the future.

6. Deteriorating culture

   1. Take the time to observe how people are showing up in meetings.

   2. Ask your team how they are doing and check in on their interactions with other teams.

   3. The most challenging part of seeing a deteriorating culture is if you are part of the deterioration. So try your best to evaluate when you are not feeling down or depleted.

7. You are no longer set up for success

   1. Assess your goals and what you think is possible with the resourcing you have.

   2. Discuss this with your boss and relevant colleagues. Understand the implications of keeping (and missing) and changing your goals and what resourcing you might need to hit them.

   3. Determine if the changes are worthwhile and likely to happen and if you are open to sticking around to see them through.

   4. If the changes aren’t something you and other leaders can agree to, decide if you want to stay on and try to hit the higher goals with less support.

8. Your function is no longer essential

   1. Do an assessment of whether your function is still essential and whether it should stand alone with an independent leader.

      • You can conduct your own review based on your understanding of the current operating needs of the organization.

      • Consider also talking with your colleagues and your boss. That might be showing your cards, but generally, the risks are low because all you are doing is uncovering what people are already thinking.

   2. If you find that it still needs to exist, then consider holding your course.

   3. If you find that it no longer should exist, consider exiting sooner.

9. You don’t believe in one or more of the leaders

   1. Be wary of your read on another leader’s job unless you understand how their function drives the company's success overall and where their weaknesses might create risk.

   2. If you truly feel concern about their ability to lead and deliver, consider talking with your boss, the CEO first, or to a trusted confidante. Be careful of gossip, you don’t want to spread your judgment widely. You want to seek out additional inputs to try to prove or disprove your take.

10. Your career goals are being significantly delayed or sidetracked

    1. Does the pace of your growth at your current company match your vision?

       • Are there enough senior posts that will be available for you to compete for?

       • Do you have sufficient sponsorship (support) from key decision-makers or influencers to advocate for you?

       • Have you planted the seeds of your desire to grow?

    2. Are you continuing to develop new skills and hone existing ones?

    3. Is your current role setting you up well for your next opportunity?

Your Turn

What are some of the signals you use to determine if your company is struggling and that it might be time to go?

Take a minute and jot them down, and build your own assessment.

And if you have time, I’d love to hear from you in the Comments section. I try to reply to every comment. Your thoughts will also help others in the Lead without Limits community.

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May you lead without limits,

Miranda was burnt out from her first class, top shelf consulting career.

The projects felt superficial, the travel was brutal, and her love life was non-existent. Granted, she was only 34, but she felt like life was passing her by.

The worst part?

Miranda always felt like she was always looking over her shoulder to see who might be ready to plunge the knife in. She wasn’t even sure that anyone was going to backstab her, but the overall culture inspired distrust. She was anxious by nature, but the job made it worse. She was constantly worried about disappointing clients, not selling enough, and whether she was climbing the ladder fast enough.

But the money always drew her back in.

Every Friday night, she would swear this was the weekend she would start looking. But after a weekend of catching up on sleep, binge-watching reality television, and retail therapy, she’d sigh on Sunday night, “Maybe I can do one more week.”

It was OK until it wasn’t.

One day, a few years later, after she had attained the coveted Partner title, it all came crashing down.

On a bright spring morning, Miranda was diagnosed with breast cancer. Her doctor warned her that the treatment was going to be intense and require time. Time that she didn’t have.

Miranda’s parents were unwell and she was spending a few days a week visiting them. She had setup additional caregiving support, but now that her own health needed attention, Miranda felt an existential pull to reassess her career and her life.

What had been an obvious path now felt like a trap. The masked misalignments that had always been there in Miranda’s lifestyle and commitments were now brightly highlighted in front of her.

Unfortunately, the time for a change was earlier. Now, with all that she had to juggle, Miranda’s only path was to wait until after the storm of her health issues passed and then craft a new path forward.

You don’t need the perfect plan. You need to prioritize figuring out what matters most.

Our biggest inhibitor to making change is fear.

Fear is what drives procrastination and avoidance. Fear reinforces the status quo and keeps you stuck. This is what happened to Miranda.

When you think about the possibility of making a change, you perhaps worry about what will happen to your career and your reputation. Will your fellow high-flying executive friends shun you? Will you miss platinum status on your favorite airline? Will you miss your fancy office and gourmet meals?

Depending upon the type of change you are looking to make and how much money you’ve squirreled away, you might not have to give up all of these perks. That said, when you leave a career, you will necessarily be leaving some of the status and people behind.

The question isn’t whether people will judge you. They will.

The question isn’t whether there are risks to change. There are.

The question is whether the status and those people who do judge you matter to you, and whether the possibility of a more aligned career and life are worth it.

Only you can answer these questions.

And when you get clear about what actually matters to you, it’s far easier to let go of the things that don’t.

Always know your non-negotiables.

The biggest mistake people make when they start to chase a dream is that they don’t get clear on their non-negotiables. These are your life essentials. Not nice to have — must-have.

It’s not as simple as reviewing your bills. Most of us could live on 30-50% less than we do.

We choose not to.

If you are like many highly successful, highly paid executives, you have gotten used to the perks that come with your paycheck. Your spending creep was gradual. It didn’t feel significant at any time, but over time, it has grown… a lot.

Perhaps it started with a nicer car and fancier meals and vacations. Then came a larger home and higher-end furnishings. The designer clothes and accessories were perhaps always present, but the volume, the refreshes and the on-a-whim purchases have only increased.

If you are serious about making a change, you need to know what your minimum looks like. This is about money, but it’s not only about money.

You want to take a look at things like where you live, what kind of home you live in, how much you want to travel, and what types of activities and support systems matter to you. If you swear by a particular fitness studio, you’ll want to make that part of your must-have list. If you are committed to a nutrition plan, you need to make room for it.

And it’s about everything that you don’t need. The gym membership that you never you. The annual friend weekend boondoggle that actually annoys you more than it excites you. The jewelry subscription that you don’t really use. Be ruthless about what you cut. If you don’t need it, taking it off the list will only give you more options.

Be thorough when you create your non-negotiables list. Don’t just plan for today, plan for the future, including retirement and surprise expenses that you simply can’t predict.

When you know your floor, you can now dream without a ceiling.

Explore as many options as you can when you start to think about what is possible and what might interest you. Don’t limit yourself too early.

We make tremendous career decisions when we are very young. It’s amazing what we ask children to choose when they are just starting to develop some sense of the world. Selecting your career path when you are in your early twenties is like asking a baby to decide where it will go to college.

Most people will work for 40+ years. That is about half of most people’s lifetime. It’s no wonder that people want to make changes 5, 10, 20 years into their careers. They have a wealth of knowledge and experiences they didn’t have when they made their initial selection.

This is why when you take a moment to pause and offer yourself a reset option, you should take it seriously and explore as wide and as far as you can. With your non-negotiables clearly outlined, you can filter that exploration with confidence. But there is no sense in reducing your options until you have evidence that proves it won’t align with what you need.

When Miranda was ready, her exploration led her down multiple paths. She considered opening up a yoga studio, becoming a product manager, and working in the arts. She wanted to work in an environment that prioritized trust and flexibility. She no longer wanted to travel. She used these along with her financial needs to filter her research and exploratory conversations and help her determine her next path.

Your network will help you find your way.

Eventually, Miranda transitioned into a COO role at a small consultancy. It wasn’t what she was expecting. After countless conversations with friends, former colleagues, and acquaintances, she was connected to the founder and CEO of the consultancy.

She had thought that leaving consulting was the answer. But when she and the CEO spoke, it became clear she had found a place where all of her non-negotiables could be met and where some of her dreams would also be possible. She didn’t actually want to leave consulting, she wanted to leave the version of consulting that she was living.

Few people know exactly what they want without a prompt. Most people need an example, an experience to help them viscerally relate to a potential path.

The best way to learn more is to talk with people — lots of people.

Your network is an endless pool of insight.

If you’ve thought about becoming an actor, go find one. If you’ve thought about moving to another country, go talk to someone who has made the move. If you’ve thought about becoming an entrepreneur, go find someone who has started their own business.

Chances are your network is wider and deeper than you think. Use it.

Even if you don’t know people who have done what you want to explore, there is likely someone in your network who knows someone who has.

A great plan without action is no better than no plan at all.

It’s easy to fall into analysis paralysis with this exercise.

There are an endless amount of datapoints to consider, people to meet, and interwoven elements. Don’t get sucked into distractions and overthinking.

Always keep your focus on the end game. You are looking for a new path.

As you talk with people, don’t just ask them open-ended questions. Ask them about your priorities, your non-negotiables, your fears. This is your chance to discover if what matters most to you is possible.

One of the ways to test what you learn, if you have the capacity and if you current job allows, is to get a side gig or do pro bono work. You won’t always be able to make this happen, and that’s OK. A class or a seminar is another option and can also give you a taste of a potential path.

The key is to get your hands dirty. If you stay in the realm of planning only, you’ll never really understand what it will take to make the change.

When you align your work with what matters most, you find that other parts of your life fall into place as well.

Miranda wasn’t starting a yoga studio or working in the arts, but she would have more time now to invest in those activities because she no longer needed to travel. In addition, the consultancy she joined had a product and technology arm that she would get to spend time with and collaborate on select projects.

Miranda moved out of her luxury apartment to be closer to her parents and to scale down her expenses. When it came down to the decision, she was surprised to find that she didn’t feel like she was giving up much. Instead, she felt relief that she was spending money on what mattered to her and no longer spending on things she could live without.

Miranda beat cancer and her health improved over time with more sleep and less stress. She realized that the stress wasn’t just from the work. It was from living out of alignment with what she valued in life.

Once she took back the reins and freed herself from her golden handcuffs, Miranda felt unstoppable.

Key Takeaways

Don’t let the goals or what attracted you in the past dictate what you do going forward. If you’re feeling doubt, don’t wait until you feel trapped. Start down this path now.

• Take stock of what matters to you

• Determine your non-negotiables carefully and thoroughly

• Explore far and wide; don’t limit your possible paths too early

• Use your network to have conversations to learn more

• Taking action is as important as making a plan, even small steps count

• When you find alignment, don’t be surprised when more pieces of your life start to fall into place

In short, you don’t have to be shackled to a job. You can find a new path, but you need to do the work to discover it.

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Bill was a consummate professional. Everyone said so.

If you needed something done, be it complicated, last minute, or taxing, he was always willing to do it and to do it well. He showed up to meetings prepared. He was inclusive and collaborative in his approach. And he was always learning, trying to improve his already robust skillset.

In short, Bill showed up every day. It’s what led to his now 7-year tenure at his current company. As the Director of Operations, he reported to the COO, and he was great at his job.

The one problem?

Over the past year, Bill had started to feel the nagging sensation of being overlooked and under-compensated. Not only were former peers now VPs and SVPs in the organization, but his MBA classmates in other companies had also surpassed him. Perhaps more importantly, Bill was starting a family and he wanted to make sure he could afford a new, larger home and still be saving for retirement.

It didn’t seem like a tall order, especially given how well he performed, but the last time Bill had been promoted was 4 years ago, and there was no sign that a promotion was going to happen this coming year.

The worst part? Bill didn’t know why it wasn’t happening.

You can’t play a game well when you don’t know the rules.

Bill had benefited from a manager earlier in his career who rewarded and recognized his great work with raises and promotions without him asking or discussing it with her.

Bill suffered from what I call “just do the work and trust the rest will come”. That might work well when you are more junior in your career, but as you rise, there are fewer senior positions to go around, which limits the number of people who can be promoted and how often that happens.

Even if you’re a high performer, that doesn’t guarantee that you’ll be the one recognized. There are many other factors at play, and your performance is only one of them.

The most successful leaders at climbing the corporate ladder are the ones who understand the process, the players, and when and how to engage themselves to influence the outcomes.

Decision makers won’t reward you unless you speak up.

Staying quiet, staying humble are beautiful qualities in high performers… for your employer.

They work well for your organization. They work less well for you.

Most organizations are in the business of maximizing profit, which means minimizing costs and maximizing revenue. You and all of your colleagues are costs, which means that the organization generally tries to minimize more investment in you. In fact, they won’t put money there unless they have to.

When executives are not aware that someone wants to be promoted, that is the same as not needing to promote them. It might feel obvious when you’ve been in a role for several years and delivering on your goals that a promotion is a foregone conclusion. It isn’t.

The days of conveyor belt career progression have long disappeared.

The only parts of a business that get increased investment are those that drive more revenue or decrease costs. This means your promotion and salary increase will only get approved if the decision-makers believe that this change will result in increased revenue or decreased costs that exceeds the cost of your promotion.

Like most humans, most senior executives resist change.

It’s much easier to stay with the status quo than to change. Only when they are enlightened with a compelling reason to change will they do so. And you shouldn’t expect someone else to advocate for you unless you have already advocated for yourself.

Understand what drives promotion decisions, and you’ll understand what you can and can’t control.

Once you’ve indicated that you’re interested in scaling the ladder, you need to understand how promotions come to be.

For most organizations, there are macro considerations:

• How is the company performing? Is it growing? Is it struggling? — This is relatively easy to understand through quarterly or monthly updates. Organizations that are growing are more likely to add additional senior-level roles to scale the organization.

• Is your function a priority investment area? — If you’re in an area where leadership is making investments, you’ll have more opportunities for advancement versus areas where they may be looking to maintain or reduce costs.

• Does a role at the next level up currently exist, and does someone occupy the role? — Unless you are being promoted into an existing position at the new level, your promotion has to make structural sense within the organization. Having you at your new level has to be a rational design choice that improves organizational design and operations. If someone occupies your target role, then you need to understand when they are likely to vacate the position, a delicate but highly important topic.

There are also individual drivers of promotions:

• What is your performance rating, and over how many cycles? — Some organizations have policies that require you to achieve a certain level rating and over a certain number of periods before you qualify.

• Do you have compensation bands, and where do you sit on them? — Are you on the upper end of your current compensation band? This might not be a reason to promote you, but if your performance is consistently stellar, it may help your case that you need to be promoted to maintain fairness in each band.

• Have you gone above and beyond in your work? — Do you take on assignments not directly under your responsibility? Are you a go-to person for strategic efforts? Your manager’s perspective matters most on this one, but the opinions of other leaders matter, too.

• Are there leadership qualities you need to exemplify? — For some organizations, you must have modeled most if not all of the leadership traits they look for at the next level to qualify for a promotion.

If you aren’t sure about any of these areas, this is your clue that you need to do some investigation and learn what matters and why.

The more you understand, the more strategic you can be in how you demonstrate why your promotion is warranted and will support the objectives of the organization.

Discover the promotion decision process to know who and when to engage.

Promotion cycles are often done annually for most organizations. But even if you know when promotions are being doled out, you might not know when the process begins.

Decisions are not formally made at the beginning, but executives generally enter the process with an informal point of view on who will secure senior posts.

Your job is to make sure your manager knows your desire to advance at least 2 years, but ideally 3-4 years before you want to achieve your promotion. Why that early? Because organizational design for senior roles is often a long-term process that takes years to realize. Without budget and operational needs aligning with a need for a higher-level role, there’s no role to promote you into.

Informal points of view are not only created through direct experience. They are formed over time by casual conversations and anecdotal stories. You can leave this process to chance. But you’ll be better served by building relationships, making your ambitions known, and demonstrating your impact and value across the organization so that the people who influence your manager and other executives are singing your praises.

Always have another option.

Some organizations simply won’t make promotions happen until their hand is forced. There may be other issues with this type of culture, but sometimes, it is simply born out of a culture of financial prudence that requires a significant, immediate risk for leaders to respond.

Even if your organization doesn’t seem to require a credible threat to consider you for a role, it’s smart to have alternative options available, even if it’s simply to leave and take time off.

There is a saying, “if you aren’t moving up, you’re moving out.” Don’t let yourself get surprised by the next restructuring or the decision of a new leader. Arm yourself with options.

Know when it’s time to move on.

Last but not least, too many leaders I know stay too long after they have gotten ample signals that they are not going to get the promotion. It’s OK to stay if the promotion isn’t what matters most to you. But if the promotion is what you want most and it’s clear you aren’t going to get it, it doesn’t make sense to stay.

One of the biggest upsides you get by speaking up and talking with your manager and other leaders about your ambitions is learning faster if your goals can or can’t be met. It’s far better to find out relatively quickly that what you want and what the organization can offer are mismatched, than to wait years hoping for an outcome that will never happen.

Once you know what is and isn’t possible, you’re much better positioned to make a more strategic move.

Key Takeways

If you’re seeking a promotion, simply doing your job well and waiting will not make it happen. Instead, take these steps to help you accelerate the process or find out that it’s time to move on:

• Share your ambition and promotion goals with your manager and other senior leaders

• Understand how your organization makes promotion decisions, including what you can control and what you can’t

• Understand the promotion decision-making process, including who is involved, their roles, and key milestones

• Create alternative options that can either force a decision from management or simply give you optionality

• Know when it’s time to move based on what you learn

Speaking up, asking questions, and taking responsibility for what you can control will help you most quickly find the best path to your next level role at your current company or somewhere else.

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Andy felt crushed.

Sydney, his number 2, his most trusted leader, his go-to person, just gave notice.

At least she was honest about why. The job no longer felt like a growth opportunity. She wasn’t learning and the business challenges felt insurmountable. Andy had known that she was ambitious, very ambitious, but thought he had more time.

What Sydney didn’t share was that she had lost confidence in Andy as a leader. He had been distracted these last few months by his own fears and overwhelm. He had started to micromanage, checking in more than was necessary, demanding detailed plans, and revisiting topics they had already discussed. Sydney and her teammates felt that he was wasting their time and distracting them from their work. Worst of all, they felt he didn’t trust their judgment.

Andy was also increasingly irritable and no longer the clear, decisive leader they had come to appreciate. He didn’t just second-guess his team, he was second-guessing his own thinking and those of his peers. Whereas in the past, you could count on Andy to be thorough while knowing when to move forward, now, his team would hesitate before bringing things to him because he was becoming an unpredictable bottleneck.

But Andy, while aware that he was more stressed lately, didn’t realize how bad it had gotten. Andy thought he was still operating the way he always had.

Sydney’s departure was a rude awakening.

Your top performers drive your team’s success. And your team’s success is your success.

It’s the classic 80/20 rule. 80% of outcomes are often driven by 20% of the talent, effort, and people. You need these special people to reach your goals.

It might feel mercenary and transactional.

But it’s the truth and if you’re a smart leader, you know this.

It’s why you fight to reward your top talent and it’s why you work so hard to find and develop top talent.

But when you are stressed, and let’s be honest, for most senior leaders these days that is a lot of the time, you tend to focus on what’s not working well. You ignore what is working well and who is driving that progress.

When things aren’t going well, leaders tend to stop focusing on their top talent. You take for granted these people who are driving most of your business, solving most of your problems, and innovating on your most promising new offerings.

These are the people who hold together your culture and strengthen your team dynamics. They can literally make or break your outcomes, which can mean making or breaking your career.

Too often, companies focus on the wrong statistic, employee retention.

Healthy companies should regularly churn out employees who no longer fit the company’s needs. A productive goal should never be about retaining all of your staff.

Retention goals should be focused on top performers.

These are the people who anchor your operations. They set the cultural tone and they set the performance bar. They are the model professionals that uplift the results and behaviors of the entire team.

It can cost more than 1.5-2x the salary to replace a top performer.

Between the lost productivity, legacy knowledge, recruiting costs and time, and the effort to onboard, this is very expensive.

It’s not just the cost of replacing a top of performer that’s a problem. Even when you finally hire a new person, you won’t know if they will work out until weeks if not months later.

It’s not worth the risk. It’s far more effective and efficient to keep your top talent.

So how do you retain a top performer?

There are many different reasons why people leave, but the most common reason is their manager.

Managers determine the trajectory of an employee. They are responsible for assigning them goals and responsibilities. They resource (or under-resource) them, develop them, and provide (or don’t provide) growth opportunities. Managers can help employees succeed and be recognized and rewarded, or they can let them languish, or even worse, hold them back.

The power that a manager has over an employee’s experience and path forward is so significant, it’s no wonder managers are the number one reason why employees leave.

It stands to reason that managers are also the number one reason why employees stay.

You might already know this, but I bet many of you reading this article are still taking the “it’s probably fine” approach, which, let’s be honest, doesn’t work.

Just because you don’t know what your top performers think of you doesn’t mean they aren’t thinking it. You are just choosing to operate blindly.

Don’t do it.

Don’t be like Andy.

Get the intel you need to understand what you need to do to retain your top talent. Even if there are truly mitigating circumstances that prevent you from keeping them, at least you will know that they are on the way out. This will give you and them the opportunity to plan a smooth transition.

Most managers don’t truly understand what matters to their top performers.

It takes time to build the trust necessary for someone to open up, to share vulnerably. One method to try is LifeLab’s CAMPS model.

Use it to get structured input from your direct reports on what matters to them and how much. Add a table to your 1:1s with employee and ask them to rate on a scale of 1-10 their satisfaction in each area (10 being the highest):

• Certainty - How much do they need to feel sure about what’s ahead?

• Autonomy - How much independence do they want in their day-to-day?

• Meaning - How do they make sense of their work and purpose?

• Progress - Are they advancing and growing at the pace they want?

• Social inclusion - Are they having the interactions they need to feel fulfilled and connected?

If you make this a part of your regular conversations — monthly or quarterly, you will get a better sense of how your people feel about their work experience, and therefore, about your leadership.

Importantly, in this model, you have an opportunity to learn more about what actually matters to your people. Getting context not just on how happy they are, but why is where this really gets interesting.

LifeLabs also recommends you ask folks for what could help them move their score up by 1 point. This is a great way to get feedback on what you can change to improve their experience.

Do this for all your employees, and use the information you learn to help you create a stronger organization, but pay closest attention to how your top performers rate their experience and why. They are what will make the biggest difference to the success of your team.

Retreating from conflict or feedback is often a sign of giving up or lack of trust.

When your top performers — the people who normally step up and step out from the rest to offer suggestions, provide critical feedback, or engage in debate — start to clam up, that’s a clear sign something isn’t right.

The issues could be personal — something in their family life, health, or other non-work items. But don’t make that assumption.

The most frequent reason why previously vocal or engaged people become silent is that they no longer believe it is worth the effort or the risk to stick out their necks.

When you see this happening, instead of getting suspicious, get curious.

Take time out of your regular schedule to spend time with your talented direct report to hear them out. Maybe add an extra 1:1 meeting or carve out more space in your existing 1:1 meetings for open discussion.

A highly structured agenda may actually shut them down further or distract them from more difficult topics like this one. Instead, ask open-ended questions and get comfortable with awkward silences. Giving them the time and space to share is of the utmost importance.

Making sure your top talent feels you are available, curious, and ready to listen is perhaps the most important way you can ensure that they don’t give up.

A shift from proactive to reactive behaviors can be a sign of distraction or disillusionment.

If you start to see your top performers get surprised or have more emotional reactions and swings, that might be a sign they are no longer operating at their best and most committed.

Generally, your top people will be more planful, more organized, and more grounded in how to respond to change and curve balls. If they are starting to feel more like a loose canon or no longer anticipating what’s ahead, they may not be feeling engaged anymore in their job.

Instead of coming down on them or avoiding confronting them on what might be happening, offer what you’re seeing as an observation and ask them if they are aware of their behavior change. Having a more light-handed, but still direct approach may create more psychological safety for them to respond honestly.

Don’t be afraid of a 360 assessment even if it takes time and is expensive.

There is tremendous value in using a 360 evaluation to signal to your team that you care deeply about their feedback.

A 360 is exactly what it sounds like — you take a snapshot of how everyone around you views your effectiveness as a leader. While not strictly focused on your top performers and their feedback, this type of assessment can surface themes about your leadership that will directly impact your top talent.

No one works in a vacuum. How your peers, manager, leaders who are senior to you, in addition to your direct reports rate your performance and offer insights around how you can improve will help your top performers as well as you. Why? Because your top performers will benefit from your strengthening your performance.

The more strategically and operationally excellent you are, the more your influence grows, the more your top talent will benefit from that halo effect, and the more you will be able to provide your top talent with growth opportunities.

These evaluations can take several weeks and be pricey, but your HR team or an outside coach or consultant can easily conduct this for you. The results could be life-changing not only in capturing valuable feedback from your top talent, but in the totality of the feedback to help you improve your effectiveness.

Once you know what your top talent wants, actively work to address the situation.

With the knowledge of what’s happening for your top performers, you can adjust how you lead, how you dole out assignments, structure and resource your team, and any other decisions in your purview that can help improve their experience while advancing business objectives.

The great news is that many times, the demands of your top talent are the demands of your staff overall and will help elevate your organization as a whole.

There will be times when you won’t be able to make a change or make it fast enough. That’s OK.

For some of your top performers, simply having an open discussion about what is realistic will help reorient them and bring back some motivation and trust.

For others, their concerns are non-negotiable. While you might not be able to retain them, with your newfound knowledge, you can now collaborate together on how to make a smooth transition. Working out in the open is beneficial for everyone.

Your top performer will be more motivated to still perform if they feel you are being supportive of their needs to transition out. You can also be more thoughtful about how you replace them as they depart. Perhaps it’s an opportunity to restructure the team or to provide another top performer with a growth opportunity.

In addition, top performers are often people you want to work with again in the future. They generally go on to do even bigger and better things over time. You may want to hire them again or perhaps your amazing direct report might become someone you might work for one day.

You never know.

Adjusting how you lead based on your top talent feedback can payoff long after you work together. It’s worth the investment to learn now what is happening and become a stronger leader now.

Key Takeaways

• Your top performers drive the majority of your results and so it behooves you to understand what matters to them and how you can improve their experience to retain them

• Seek out to understand what matters to them regularly. Try the CAMPS method or find one that works for you

• Watch for signs of waning interest, engagement, or a reluctance to speak up. They are early signals worth paying attention to

• Consider a 360 assessment as a way to support not just your growth, but how you can be a better leader on behalf of your top performers

• Even if you cannot retain a top performer, creating a safe space to have open and honest dialogue will allow you to plan together and mitigate risk. It will also allow you to maintain a strong relationship with someone who you likely want to work with again in the future

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It was 3am and we were 6 hours away from a press conference where we were supposed to demo our product.

But the product didn’t work… yet.

Our leaders had set a deadline without verifying with the operational and technical teams if it was a realistic timeline. And it wasn’t just a deadline, it was a very public deadline where if we didn’t make it, the broader world would know.

I was working at NBC to build the first-ever online video syndication unit. Our leaders were smart, ambitious business strategists with zero technology build-out experience.

Lucky for them, they hired people on their team that did — people like me and my managers. We worked nonstop for months, 16-18 hour days, 7 days a week to prepare for this arbitrarily, randomly scheduled launch.

My managers might not have been freaked out, but I was. The only reason why I pulled those hours was because failing this was tantamount to setting myself up to get fired.

So what happened at the press conference? Did we manage to get a product that wasn’t fully built fully built in 6 hours?

Well, it definitely wasn’t fully functional, but we were able to demo parts of the product to give the appearance of something worked.

What ultimately happened to that product?

From the precipice of disaster, after many more months of work and a much larger team, it became hulu.

Worrying about failure leads to inaction which is the only guaranteed way to not succeed.

When I think back on that story today, I no longer feel incredible frustration with the leaders who made impossible promises and then weren’t the ones staying up all night to make them happen.

They didn’t model my version of leadership, but they also did something I was far too afraid to do — envision something entirely new and get people excited enough to fund it.

They took the leap that so many others never do.

Instead of only thinking about an idea, investigating an idea, and talking about an idea, they actually did something to advance the idea.

If you spend your time worrying and never give your idea a go, how can you ever be successful?

Our relationship to failure bears investigating.

When I learned in college that 90% of startups fail, I took that as a clear signal to never become a founder.

To be fair, I had already developed a bias against starting my own business. My father is a serially unsuccessful entrepreneur. I don’t mean to be derogatory. It’s just a fact. He tried over and over again, but none of his ideas took off.

To me, being a founder felt like a guaranteed way to overwork with failure guaranteed on the other side.

And yet being part of a startup, an early member of the team somehow didn’t feel as scary. I loved being an early employee. It meant I was able to have a significant impact on strategy, execution, and the organization’s culture.

For some reason, in my mind, the risk of failure was diminished if I wasn’t the inceptor of the idea.

It doesn’t make much sense. Starting the startup was too scary, but being part of a startup wasn’t?

I, like many people, don’t have a rational relationship with my fear of failure.

In fact, in much of my life, I have been rather fearless.

One of my earliest bets was in high school.

After my middle school art teacher shared a newspaper clipping with me about a new technology-driven magnet school that was opening in the fall of my 8th-grade year, I was intrigued.

It didn’t bother me that it was unproven. It didn’t matter that there was only one class before me. The vision was intoxicating — a school where every student would get a new computer to take home ever year on loan along with a modem. We would take college level science and math courses. School would be from 8am-4:30pm and at the end of 4 years, we would have attended school for the equivalent of 5 years.

It sounded amazing.

In 1992, I became a member of the second graduating class of what is now called the Bergen Academies.

When I attended, the school still had to market itself heavily to get parents and students to apply. Today, the school is regularly ranked as one of the top of the high schools in the U.S. and the entrance exam starts blocking a local highway at 6:30am on a Saturday morning because there are so many students trying to apply.

What was my reward for taking a chance to go to this school?

I was able to influence the curriculum, the programming, and the activities. I was part of the early group of students who established the school as legitimate in the eyes of the top universities in the country.

I was able to gain acceptance into schools like Stanford, Princeton, and the University of Pennsylvania not just because of the rigorous coursework, but also because I could tout things like being on the varsity soccer team and playing in the flute ensemble — both being the result of being part of an incredibly small school where I was one of only a few students who even wanted to play soccer or flute. I wasn’t strong at either, but there was literally no one else who could play.

These types of risks and rewards played out throughout my career and life.

• The start-up unit at NBC that became hulu gave the opportunity be part of a company that changed the media landscape

• Joining an e-commerce startup resulted in my first CEO appointment

• Choosing to be an early adopter of online dating allowed me to meet my husband, someone who I would have never met otherwise

• Restarting oil painting last year, after a 35-year hiatus, allowed me to discover a latent talent that I didn’t know existed

But my life hasn’t been all fearless decisions.

In 2019, as my family was contending with extreme sleep deprivation over multiple years, and I was embarking on a major revenue transformation at my company, I became paralyzed with fear… daily.

I found it difficult to make decisions and I second-guessed everything I did. I incessantly asked for feedback and input and often delayed key actions until there were negative impacts.

My body was perpetually in fight or flight. I assigned unreasonably high stakes to everything at work and was unwilling to ask for help as I struggled to keep my head above water.

When the pandemic hit in 2020, that only exacerbated my fear response. I was a high-functioning, anxiety-ridden leader who was charging into burnout.

I held it together because I perceived I had to. But when I look back at how I navigated that period in my life — including the few years that followed, I can see how much of what I did and didn’t do was all driven by fear of failure.

Give yourself the space to assess the level of risk before you go into decision-making mode.

What I wasn’t able to do during that difficult period was distinguish the level of risk of each of my actions and the context around me. Sleep deprivation and other forms of trauma can do that do you.

When you lose perspective, it’s easy to be cavalier when you should be conservative or be overly cautious when you should be more aggressive.

I tended towards being overly cautious, but sometimes fatigue can take you in the other direction and before you know it, you’ve rushed a decision that should have been handled with more care.

When a negative outcome is significant and permanent, you might need to be more thoughtful. Examples include marriage, having kids, getting surgery, making a big investment or doing substantial cost-cutting.

But most decisions aren’t likely to lead to extreme outcomes.

The only way to properly understand the risk is to give yourself room to step back from your emotions and with a more calm perspective, make your assessment. Some great ways to do that include:

• Take a walk to move your body and let your emotions flow through you and not drive you

• Meditate. Breathing mindfully and observing your thoughts instead of being swept up by them can help you get the perspective you need

• Journal. Writing out your worries and observations can help you make more sense of the issue

• Sleep on it. Your subconscious can do an incredible amount of processing if you give it time to work through what your conscious mind cannot

Define failure with the people who matter most before you make your own assumptions.

What may feel like a failure to you may not be viewed the same way by someone else. When I was in the throws of self-doubt at work, my boss, the CEO came to me numerous times to help me recalibrate my orientation toward failure.

A simple way to do is the “and what if that goes badly?” exercise. When you have something that you perceive is high stakes, find someone you trust and have them ask you “and what if that goes badly?” and you answer. You repeat it over and over and over again until you get to a point where there is no other answer.

You’ll find that most issues will end up with “and it’ll be OK.” By talking it out, you can get a second opinion about whether your assessment of risk is accurate and whether your fear of failure is out of line. This is particularly helpful when you are overly fearful.

What you do after you fail is far more important than the fact that you failed.

In the end, it’s important to remember that failure is not only a part of life, but it’s part of how we develop. We don’t chastise babies for dropping things, toddlers for falling as they learn to walk, or young children for stumbling as they master new skills. Only through failure can they learn.

Everyone fails. That is just a part of life.

Part of what we learn when we are young, and sometimes lose when we get older is the perspective that failure is necessary and helpful to our development as leaders, as adults, and as humans.

Those who know how to pick themselves back up, learn from the fall, and then get back in the game are the ones who will ultimately succeed.

Here are some of the ways I bounce back from failure:

• Remind myself that the journey is what matters and that through failure, we can find our way to success

• Find the learning in what took place and commit to incorporating the learning into my behaviors

• Talk about and share my misses so that others can learn alongside me

• Do an activity I love and remind myself that one failure isn’t going to make or break my vision or path forward

Your biggest failures are simply your biggest learnings.

How fast you can learn from a miss is how fast you can grow and improve and reach your goals. It’s OK if it takes you longer to navigate certain periods of fear and self-doubt.

As we get older and become more senior as a leader, we often face more complex issues with more variables.

Learning curves are not linear. Expect to get knocked down a few rungs at times. When that happens, just remember that it’s not a sign you have lost your touch or your ability to be effective. It’s a sign that you are ready for a deeper, more fundamental growth moment.

The deeper the challenge, the greater the growth. I like the visual of a deep pit. When you fall into a pit, the deeper the pit, the more capable you have to be to get out of it.

For me, it took me leaving my last company and last role to create the space I needed to reorient myself to my fear of failure. I also needed my family to move to a healthier place in terms of how we were all sleeping. It’s still not 100%, but it is remarkably better than it was 6 years ago.

My creativity has returned and my sense of possibility and playfulness has reentered how I do my work and engage with the people around me.

I am not the same as I was before facing my deep fears of failure.

I am stronger. You will be, too.

Key Takeways

• Worrying about failure leads to inaction which is the only guaranteed way to not succeed

• Our relationship to failure bears investigating. Don’t be surprised if your thinking isn’t rational

• Give yourself the space to assess the level of risk before you go into decision-making mode

• Define failure with the people who matter most before you make your own assumptions — their perspective might be the information you are missing

• What you do after you fail is far more important than the fact that you failed

• Your biggest failures are simply your biggest learnings

Take a moment this January and reflect on your relationship to fear of failure. Tell me what you discover!

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May you lead without limits,