How Mike Fisher Stopped Starting Over: The Skills You Built May Be the Key to Your Next Chapter

Your next career move may not require a new identity. It may require seeing the value in the one you already built.

We’ll Discover

• Why career transitions are often less about starting over and more about recognizing transferable skills.

• How unlearning can be just as important as learning when you move into a new environment.

• Why the hidden market rewards people who are known for something specific.

• What leadership, resilience, focus, and adaptability have in common across very different careers.

• How to think about your next chapter in terms of skills and problems you can solve, rather than simply the next title you want.

There is a point in many careers when the question stops being, “What have I accomplished?”

You already know the answer.

You have the title. The experience. The relationships. The years of hard-earned judgment. You have probably solved problems that once felt impossible and navigated situations that would have overwhelmed the person you were ten or twenty years ago.

And yet, when it is time to think about what comes next, many accomplished professionals do something surprising.

They start over.

They look at the next role as if everything they built before it belongs to a different version of themselves.

I thought about that throughout my conversation with Mike Fisher, CEO of MyFitnessPal.

Mike's career has moved across military leadership, technology, entrepreneurship, consulting, CTO roles, and ultimately the CEO seat. On the surface, those chapters might look disconnected.

They aren't.

The interesting part of his story isn't the list of companies or titles. It is what he carried from one chapter into the next, what he had to unlearn along the way, and how opportunities continued to find him because of what people knew him for.

That is a very different way to think about a career.

Your Experience Doesn't Become Irrelevant When Your Context Changes

Mike shared something that immediately resonated with me because I have experienced it myself.

When he left the military and became a software engineer, he initially thought of his military experience as something that was finished. He had served. That chapter was closed. Now he was a software engineer.

Then a manager saw something he wasn't seeing yet.

She pointed out that the leadership and management experience he had gained in the military could be applied in this new environment. That conversation changed the trajectory of his career.

I understand that instinct to compartmentalize because I did the same thing.

For years, I barely talked about my own military background. I had moved into technology, startups, entrepreneurship, and leadership, so I assumed the earlier chapter wasn't relevant anymore.

Then someone introduced me as the “F-16 girl.”

And I remember thinking, How is that related to what I'm doing now?

It turned out to be very related.

It was part of what made my story different.

That is the mistake I see people make when they enter a transition. They look at their previous experience through the lens of the job they had, rather than through the lens of the capabilities they developed.

Leadership is transferable, and so is strategic thinking. 

Learning how to operate under pressure is transferable.

Building relationships, solving problems, making decisions with incomplete information, navigating change, communicating clearly, and taking responsibility do not suddenly disappear because you changed industries or job titles.

Sometimes the most valuable thing you bring into your next chapter is something you stopped thinking about years ago.

The Career Transition May Require Unlearning, Not Just Learning

There is another part of Mike's story that I found particularly relevant for experienced leaders.

When he moved from the military into the civilian world, he had to unlearn some of what had made him effective before.

In the military, a leader can give a lawful command and expect it to be followed. In a technology company, that same approach has limits.

Mike described leadership as having a kind of “glass gavel.” You can use command when you need to, but if you keep hitting the gavel, eventually it breaks.

That idea extends far beyond the military.

Every successful career teaches you behaviors that work in a particular environment.

The problem is that we can become so good at those behaviors that we forget to question whether they still serve us.

The decisive leader may need to become a better listener.

The expert may need to become more comfortable asking questions.

The person who built everything themselves may need to learn how to build through other people.

The executive who thrives on constant change may need to understand that not everyone experiences change as energizing.

Mike learned that last lesson early in his leadership career. He loves change and sees it as an opportunity, but he realized that other people may experience the same change through uncertainty, fear, or the possibility of failure. That awareness changed how he approached organizational changes later in his career.

That is what growth at a senior level often looks like.

Not becoming a completely different person.

Becoming more intentional about which parts of yourself you bring into the room.

Stop Thinking About the Next Title. Start Thinking About the Next Skill.

One of the strongest ideas Mike shared was also one of the simplest:

Think about skills, not titles.

When people plan their careers, they often create a ladder in their heads.

Manager. Director. VP. CTO. CEO.

But titles are the outcome. Skills are what create the possibility.

Mike suggested thinking instead about the capabilities you need to develop: running a P&L, managing a larger organization, leading a transformation, managing a budget, building teams, or taking on responsibilities that stretch beyond your current role.

I love this way of thinking because it changes the question.

Instead of asking: What title should I pursue next?

Ask: What do I need to learn how to do next?

That question creates far more possibilities.

You may discover that you don't need to leave your current company to develop that skill.

You may find a project that gives you exposure to a part of the business you've never touched.

You may volunteer for a transformation, take on a commercial responsibility, advise a startup, teach, join a board, or work with someone outside your normal function.

Those experiences become what Mike called “side quests.”

And sometimes those side quests become the most important parts of the career.

Your Reputation Can Open Doors Your Résumé Never Will

Mike also gave a very clear example of something we talk about constantly at LEAP: the hidden market.

He told me he has applied for only one job in his entire career. Most of his opportunities came because someone knew him, recommended him, or knew what he specialized in. His consulting company operated largely through word of mouth because people understood what the firm was known for.

That is not an argument against résumés.

It is a reminder that your résumé is only one representation of your career.

Your reputation is working in places your résumé cannot reach.

Someone remembers that you are exceptional at scaling organizations.

Someone else remembers that you know how to navigate a complicated transformation.

Another person remembers how you lead during a crisis.

Another remembers that you can walk into a messy problem and create clarity.

Those memories can become opportunities.

Mike's own path to MyFitnessPal illustrates exactly how this works. A search firm initially contacted someone else about a CEO opportunity. That person wasn't interested, but recommended Mike. The original opportunity didn't work out, but the conversation eventually led to MyFitnessPal.

The opportunity didn't begin with an application.

It began with someone saying:

You should talk to Fish.

That is the hidden market.

And it is why I keep encouraging experienced professionals to ask not only, “What am I qualified for?” but also, “What am I known for?”

Focus Doesn't Mean Having Fewer Ideas

Another part of our conversation stayed with me because I know this tension personally.

Experienced, ambitious people often have no shortage of ideas.

The challenge isn't generating possibilities.

It is deciding which ones deserve attention.

At Etsy, Mike saw firsthand what focus could do when the company needed to accelerate growth. Leadership narrowed attention around a critical business metric rather than allowing the organization to continue spreading resources across numerous side projects.

But Mike made an important distinction that I think is easy to miss.

Focus does not have to look the same at every level of an organization.

When a company is in crisis, focus may need to move higher and become more concentrated. In healthier periods, senior leaders can create room to explore while individual teams remain focused on their own priorities.

That applies to careers too.

You do not need to pursue every possibility just because you can see it.

You can remain curious while still being selective.

You can explore without constantly changing direction.

And you can permit yourself to have ideas that are not immediately turned into projects.

Sometimes the most strategic career decision is deciding what not to pursue.

The Hard Parts Are Training, Too

Mike's ultra-marathon experience might seem like the least career-related part of our conversation.

I actually think it was one of the most relevant.

He talked about the “dark moments” of long races, when the body is exhausted, the night is long, and continuing requires something beyond motivation. For him, the experience has become a form of training for the other difficult things life will inevitably bring.

That perspective changes how you think about difficult periods.

A failed interview can be feedback.

A business idea that doesn't work can be information.

A career transition that takes longer than expected can teach you something about what you actually want.

A difficult leadership experience can expose a behavior you need to change.

The point isn't to pretend those experiences are easy, because they aren’t. 

The point is to stop assuming that difficulty means you are on the wrong path.

Sometimes you are simply in the part of the journey where you are being asked to build a capability you did not have before.

And there is another lesson from Mike's ultra-marathons that I think ambitious people especially need to hear:

You don't go through the hard parts alone.

Even when he is physically alone on a trail, he knows there are people at the next aid station, people waiting at home, people running alongside him, and people supporting him along the way. He connected that directly to entrepreneurship and leadership: you need a team around you that you trust and that trusts you.

There is strength in independence.

There is also strength in knowing when you need other people.

What AI Changes and What It Doesn't

We also talked about something almost impossible to avoid right now: AI.

Mike's perspective was optimistic, but not naïve.

He sees AI as a powerful tool for solving customer problems faster, while also acknowledging that the transition creates real disruption and uncertainty. His point about technology was that new capabilities often make previously impractical ideas possible. He gave the example of building an app for an ultra-marathon that previously would not have been worth the effort to develop.

That made me think about careers differently.

When technology changes, the question is not only:

What jobs will disappear?

It is also: What becomes possible now that wasn't possible before?

That is a much more useful question for someone trying to build a career.

AI may change how we work.

It may change which skills are valuable.

It may change how companies are structured.

It may create new businesses and eliminate others.

But the underlying challenge remains remarkably familiar: 

Can you identify a problem that matters and create value by solving it?

That is true whether you are leading a company, looking for your next role, building a consulting practice, advising a founder, or figuring out what your next chapter looks like.

Your Next Chapter May Already Be Hiding Inside Your Last One

That is probably the biggest takeaway I took from my conversation with Mike.

His career looks unconventional if you only look at the titles.

Army captain and pilot. Software engineer. Engineering leader. PayPal. Entrepreneur. Consultant. CTO. CEO.

But the story becomes much more coherent when you look at the capabilities underneath it.

Leadership. Technology. Scaling. Problem solving. Transformation. Building teams. Making decisions. Learning. Adapting.

And, perhaps most importantly, knowing what he was good at and continuing to find new places where those capabilities could create value.

That is what I want more experienced professionals to see when they look at their own careers.

You don't necessarily need to reinvent yourself from scratch.

You may need to recombine yourself.

Take the expertise from one chapter and apply it to a different problem.

Take the leadership experience you built in one industry and bring it somewhere unexpected.

Take the relationships you've accumulated over twenty years and activate them differently.

Take the skill you developed almost accidentally and realize it has become one of your greatest assets.

Your career may not need another rung on the ladder.

It may need a new way to use everything you've already built.

And sometimes, the next opportunity begins when someone who knows your work says:

“You should talk to them.”

A Question to Take With You

If you stopped looking at your career as a sequence of titles and started looking at it as a collection of skills, relationships, experiences, and problems you know how to solve, what could you do next that you haven't considered yet?

Key Takeaways

• Career reinvention does not always require starting over; your existing experience may contain the capabilities that create your next opportunity.

• Skills often transfer across industries, functions, and career stages even when job titles do not.

• Every career chapter teaches you something, but some transitions also require you to unlearn behaviors that worked in your previous environment.

• Building a reputation around what you are genuinely good at can create access to opportunities that never appear on a job board.

• Thinking about your next career move in terms of skills rather than titles can reveal opportunities you would otherwise overlook.

• Focus is not about eliminating curiosity; it is about deciding where your attention can create the most value.

• Difficult experiences can become training for future challenges when you take the time to learn from them rather than simply move past them.

• AI is changing how work gets done, but the ability to identify meaningful problems and create value remains central to career opportunity.

Frequently Asked Questions

What does Mike Fisher's career teach us about career transitions?

Mike Fisher's career illustrates how experience can transfer across very different environments. His military leadership experience became relevant in technology, his technology background contributed to executive leadership, and his consulting and operational experience created additional opportunities. The larger lesson is to look beneath job titles and identify the skills and judgment you can carry into a new context.

How can I identify my transferable skills?

Look beyond the responsibilities listed in your job description. Consider the problems people consistently ask you to solve, the situations where others rely on your judgment, the capabilities you developed through difficult experiences, and the results you have repeatedly produced. Those patterns often reveal transferable skills more clearly than your title does.

Why is reputation important during a career transition?

Your reputation can connect you to opportunities before they become formal job openings. When people know what you are particularly good at and understand the problems you can solve, they are more likely to think of you when an opportunity emerges. Mike Fisher's career is a strong example of this hidden-market dynamic.

Should I focus on skills instead of job titles when planning my career?

Titles still matter, but skills can provide a more useful framework for deciding what experiences you need next. Instead of focusing only on becoming a particular title, identify the capabilities that role requires and look for opportunities to develop them. That can open paths that a traditional career ladder might not reveal.

What does unlearning have to do with career growth?

The behaviors that make you successful in one environment may not always work in another. Career growth can require recognizing which habits, assumptions, or leadership approaches served you previously and determining whether they still fit the people, culture, or responsibilities you are navigating now.

How can I use the hidden market in my own career?

Start by becoming clear about what you want to be known for, then make sure the people in your network understand it. Reconnect with former colleagues, clients, peers, and other professional relationships. Have conversations before you need something, share what you are thinking about, and make it easy for people to understand the problems you can solve.

How should experienced professionals think about AI and their careers?

Rather than focusing only on which tasks or roles AI may change, consider what new problems, businesses, services, and ways of working become possible because of it. The more clearly you understand the value you create and the problems you solve, the easier it becomes to think strategically about where technology fits into your next chapter.