How I Keep My Ambition Growing (And How You Can Too)

When I think about ambition, I don’t start with business. I start with a field of frozen corn.

I was about 11, walking across our family’s farm on a cold winter afternoon. The stalks were down, the snow was crunchy, and a DC-6 flew over on its way to Chicago. At that moment, a question hit me so hard, it felt almost religious: How far can I go?

That question has been on my mind ever since.

In a recent 10xTalk podcast episode with my co-host Joe Polish, we unpacked what entrepreneurial ambition really is and how to turn it into a bigger future instead of burnout. This is my recap of that conversation, with an invitation to go even further with Strategic Coach and harness your lifelong ambition.

Ambition isn’t a fuel tank.

A lot of successful entrepreneurs secretly worry they’re going to “run out” of ambition. The story they’ve absorbed is that you push hard in your 30s and 40s, cash out in your 50s or 60s, and then coast.

If you’re already feeling stuck as a successful entrepreneur, that story will make you even more nervous.

That’s never matched my experience.

Over 50 years of coaching, I’ve seen ambition behave less like a fuel tank and more like a capability. You start with a question—How far can I go?—and every time you act on that question, you’re forced to develop a new capability. You learn something, create something, build a new relationship, or adopt a new tool. That new capability produces results, and those results increase your ambition. It turns into a loop: ambition → capability → bigger ambition.

Why retiring from your ambition doesn’t work.

On the podcast, I told Joe I’ve never met a happily retired entrepreneur.

I’ve met happy entrepreneurs who have redesigned their roles, gained greater business freedom, and developed a different kind of entrepreneurial vision. But the ones who try to retire from being who they are rarely stay happy for long.

One reason is structure. A company gives you deadlines, commitments, and a place to put your energy and identity. Those things keep you young. When you retire, you trade lots of small deadlines for one big deadline at the end.

I’ve never found that very appealing. I like having a lot of deadlines between me and the big deadline.

Most ambition doesn’t “run out”; it gets traded for a sense of safety. But when you eliminate risk, you also eliminate excitement, curiosity, and creativity—and that’s when you start asking, “Why am I overwhelmed as a business owner?” even though, on paper, you’ve already won.

One of the biggest shifts we make in Strategic Coach is getting entrepreneurs out of activities they’re bad at or hate doing and into what we call Unique Ability—the work they’re excellent at, love doing, and can sustain for a very long time with increasing energy. When your days are designed around Unique Ability, your ambition has a clear outlet. The same drive is there, but it’s finally running through a much better system.

Where the weird go to get wired.

Another theme from my conversation with Joe is environment. Ambitious entrepreneurs often feel like the “weird ones” in their existing circles. They’re told to calm down, be reasonable, or stop talking about a future that’s bigger than the past. The isolation that results from that is one of the quiet mental challenges of entrepreneurship.

We built Strategic Coach to be the opposite of that. In the episode, I shared a line that came out of a client discussion: Strategic Coach is “where the weird go to get wired.” Our workshops, communities, and tools are designed so you can have the conversations you can’t have anywhere else. You’re surrounded by people whose ambition and values match yours, so you don’t have to edit yourself.

When you combine that kind of peer group with clear thinking tools, delegation, and better decision making, your ambition stops feeling like a problem you need to manage. It becomes an asset you’re proud to grow.

Extending your lifetime—and your future.

The last idea Joe and I explored is called The Lifetime Extender. I ask entrepreneurs to take the age they quietly assume they’ll be “done” by and add 25 years. Then we have them describe what it means to be healthy, sharp, and fully engaged at that advanced age.

For many entrepreneurs, just doing this once immediately changes their thinking. Instead of compressing everything into a shrinking window, they suddenly have decades of new possibilities.

Their decisions shift from “How do I wrap this up?” to “What kind of business strategy and growth do I want if I’m still creating value at 95 or 100?”

In my own case, I’ve set a productive lifetime goal of 156. I don’t know the exact number I’ll reach, and that’s not the point. The point is that thinking this way gives me a sense that time is expanding. I have room to keep building capabilities, launching new offerings, and supporting entrepreneurs.

My ambition is higher and calmer in my 80s than it was in my 30s because my future is bigger, not smaller.

Giving your ambition a bigger, better future.

If you’re an entrepreneur who’s already successful on paper but feels stuck, restless, or a bit lost, there’s nothing wrong with your ambition. What’s missing is structure.

Here’s the structure I’ve seen work best:

• Treat ambition as a capability you can keep growing.
• Refuse to retire from who you are.
• Build your days around Unique Ability instead of weaknesses.
• Put yourself in rooms “where the weird go to get wired.”
• Extend your personal time horizon.

Do that, and your ambition becomes one of the safest, most energizing parts of your life. It gives you freedom, a clearer entrepreneurial vision, and a future that’s genuinely bigger than your past.

If you’re ready to give your ambition a clearer path in 2026, let’s talk about it. A Strategic Coach Discovery Call is an opportunity to reflect on where you are now, where you want to go, and whether our program is the right framework for your next level of growth. Book a call with our team.