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What Founders Can Learn About Letting Go: From Runner to Jogger

Sep 24
3 min read

I'm (now) a Jogger.


For the better part of 40 years, you could find me logging thousands of miles on the road during each of the four seasons. Snow in January. Humidity in July. Rain in April. Crunching leaves in October. I was always training for something: a marathon, a half marathon, or a week hiking in some distant corner of the world.


If you called me a jogger, I'd correct you, politely but firmly. "I'm a runner!" Jogger was an insult, a word for people who weren't serious.

I'm (now) a Jogger. People's legs as they run.
The hardest part is letting go of the label. Runner. Founder. CEO.

The sands of time have a funny way of settling these debates. Over the last few years, I've become a jogger. Some days a walker. And here's what surprised me. I'm not in mourning.


I feel gratitude for the passion to get out four decades later and move. A long jog on a crisp morning now gives me the same joy a 20-mile run once did. Maybe more, because I'm no longer chasing a split time. I'm simply present.


I think about this often because I see the same struggle in nearly every founder from which I sit across.


For 20 or 30 years, they've been the runner. The top dog. The person every decision flows through. Their identity and their company have grown together until it's hard to tell where one ends and the other begins. So when the conversation turns to selling, the fear is not always about valuation or deal structure. It's about the question underneath: who am I if I'm not running this thing?


Arthur Brooks tackles this in his book From Strength to Strength. He describes two kinds of intelligence. Fluid intelligence, the raw speed and problem-solving horsepower of our younger years, tends to peak early and then decline. Crystallized intelligence, the wisdom and judgment built from experience, keeps growing well into later life. Brooks argues that the unhappiest people cling to the first curve long after it's turned. The happiest make the leap to the second.


Founders who sell well seem to get this intuitively. They recognize the energy needed to scale their business through its next phase may belong to someone else, whether that's a strategic buyer or a private equity partner with fresh capital and a new playbook.

That recognition isn't defeat. It's wisdom.


What comes next can be remarkable. I've watched former owners become mentors, board members, investors and advisors. I've watched them spend time with grandchildren they barely saw during the building years. Some start something new. Others finally take the trip they kept postponing. They trade the marathon for the long walk and discover it has rewards of its own.


The hardest part is letting go of the label. Runner. Founder. CEO. Once you release it, you realize the label was never the source of the joy. Moving forward was.


If you're a founder wrestling with that transition, I get it. I've lived my own version of it as a 4x founder and on the pavement. The next chapter isn't a smaller life. It's a different one, and it can be every bit as fulfilling.


Keep moving.



What founders can learn doesn't end with learning to to let go and move forward. Talk to our team today to explore M&A and discuss everything you need to know before entering the market. Visit www.itexchangenet.com/contact-us.

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