When I was younger, ambition was pretty easy to define. Get the next opportunity. Make more money. Earn the title. Build the résumé. Prove that I could do the job, then prove that I could do the job above that one.

There was always another rung on the ladder, and for a long time, climbing it felt like progress. At 43, ambition feels very different.

Over the past year, I've found myself essentially starting over professionally. After more than two decades building a career that took me from the classroom into educational technology, cybersecurity, transportation, sales, and leadership, I made the decision to take everything I had learned and put it toward building companies of my own.

Some days that feels incredibly exciting. Other days I wonder what in the world I was thinking. I suspect that's part of the reality we leave out when we talk about entrepreneurship and career changes later in life.

Starting at 43 isn't starting at 23

There's a popular image of entrepreneurship that still revolves around youth: the twenty-something founder with very little to lose, working ridiculous hours and betting everything on an idea.

The actual data tells a much more interesting story. Research published in HarvardBusinessReview, using U.S. Census Bureau data, found that the average entrepreneur was 42 when founding a company. Among the top 0.1% of startups based on growth during their first five years, the average founder was 45. The researchers also found that relevant industry experience substantially increased the likelihood of entrepreneurial success.

That surprised me when I first came across it, but living it makes the finding seem almost obvious. By your 40s, there's simply more at stake. Many of us have mortgages, marriages, retirement accounts, established careers, reputations, families, and financial responsibilities that didn't exist in our 20s. The Bureau of Labor Statistics reported that workers ages 45 to 54 had been with their current employer for a median of seven years in 2024. Walking away from an established path at this stage isn't just changing jobs.

For many people, it means disrupting something they've spent years building. You also know enough about the world to understand exactly how badly things can go.

At 23, I could look at an idea and immediately see everything that could go right. At 43, I can see everything that could go right, everything that could go wrong, what it will probably cost, who needs to be involved, where the operational problems will appear, and at least six reasons why the original timeline is unrealistic.

Experience is incredibly useful. It is also occasionally exhausting.

But you're not actually starting from zero

This is probably the biggest misconception I've had to work through myself. When you make a significant career change later in life, it can feel like you're leaving everything you built behind.

You're not. I spent eight years as a teacher. At the time, I certainly wasn't thinking, "This will be excellent preparation for entrepreneurship." Looking back, though, teaching taught me how to read a room, explain complicated ideas simply, adapt quickly when a plan isn't working, and understand that different people are motivated in completely different ways.

Then I moved into sales. Those years taught me how to listen, negotiate, build relationships, handle rejection, identify problems, manage long sales cycles, and keep moving when something I was certain would close suddenly didn't.

Leadership and operations added another education, much of it through mistakes. I learned to think about what happens after somebody sells the big idea. I learned that every industry believes its problems are completely unique when many of them are remarkably similar.

Research on entrepreneurship suggests that this accumulated experience matters. Earlier Kauffman Foundation research into U.S. technology entrepreneurs found an average founder age of 39, with twice as many founders over 50 as under 25. Another Kauffman study of high-growth entrepreneurs found that founders were about 40, on average, when they started their first companies.

So maybe "starting over" isn't quite accurate. You're starting with inventory: relationships, mistakes, skills, failures, successes, perspective, and a much clearer understanding of what you're good at and what you're absolutely not good at.

You have scars, but you also have tools.

Success starts to mean something different

This may be the biggest change I've noticed in myself. When I was younger, a lot of my ambition was about proving that I could be successful. I'm considerably less interested in proving that now. I'm more interested in deciding what success should actually look like.

For years, many of us inherit definitions of success without really questioning them. A bigger salary is better. A bigger title is better. A bigger company is better. More responsibility means you're moving forward.

Eventually, you realize that "more" and "better" aren't synonyms. Psychologists studying midlife have pushed back against the old idea that these years are primarily a period of decline or crisis. Margie Lachman, a lifespan-development researcher at Brandeis University, describes midlife as a period that can bring greater confidence and resilience while also forcing us to navigate competing roles and make decisions that shape the decades ahead.

That resonates with me. Building Destinations & Detours and Super Storm Events has certainly made me think about growth, revenue, profitability, and scale. Those things matter. But I've become equally interested in how we build.

I want to work with people I genuinely enjoy working with. I want ideas to be welcomed regardless of someone's title. I want people to have room to experiment, fail, learn, and try again. I want customers to feel like human beings rather than transactions, and I want us to create opportunities for the people building these companies alongside us to pursue their own definitions of success.

Twenty years ago, I probably would have measured the dream primarily by how big the company became. Today, I'm just as interested in what kind of company it becomes.

You stop performing ambition

Getting older has brought another unexpected benefit: I'm much less interested in looking impressive. I'm more comfortable saying, "I don't know." I'm also more comfortable surrounding myself with people who are better than me at something. In fact, I'm actively looking for them.

If I'm the best person in the company at marketing, operations, sales, technology, finance, travel planning, event production, and everything else, I haven't built a great company. I've built myself a very stressful job.

The ambition now is to create something that becomes bigger than what any one of us could build individually. That requires collaboration, trust, humility, and occasionally getting your ego out of the way.

I'm still working on that last one.

Maybe we're not starting over

Career researchers increasingly describe modern careers as nonlinear, with transitions involving not only a change in work but a change in professional identity. A 2026 review in the AnnualReviewofOrganizationalPsychologyandOrganizationalBehavior describes careers as increasingly involving these kinds of transitions rather than one uninterrupted professional path.

Maybe that's a healthier way to look at it. The teacher is still here. The salesperson is still here. The leader who made good decisions is here, along with the guy who made some spectacularly bad ones. Every company, manager, customer, colleague, lost deal, successful project, and unexpected turn contributed something to what I'm building now.

At 43, I'm not starting from the beginning. I'm starting from experience. At 23, I wanted to find out how far I could go. At 43, I'm much more interested in deciding where I actually want to go, who I want beside me when I get there, and whether we can build something meaningful along the way.

That's a different kind of ambition. And I'm pretty excited to see where it leads. #Entrepreneurship #CareerChange #MidlifeCareer #Leadership #FounderJourney #CareerPivot #ProfessionalGrowth #StartingOver #EntrepreneurMindset #BusinessLeadership #CareerDevelopment #SmallBusiness #StartupLife #PersonalGrowth #SecondAct #Entrepreneurs #BusinessOwner #LeadershipDevelopment #CareerTransition #ProfessionalDevelopment #Founders #BuildingABusiness #SmallBusinessOwner #LifeAfter40 #PurposeDrivenLeadership