The memory is clear as day: standing at the starting line just after sunrise, the air warming up alongside my calf muscles. I’m surrounded by 2,500 other athletes, waiting for the cannon to signal the start of an Ironman. My heart rate is already 140, and I haven't even started swimming yet.
In that moment, despite having built multiple businesses and raised five kids, I felt more vulnerable than I had in years.
And that's exactly why I was there.
The Comfort Zone Is Where Leadership Dies
As CEOs and entrepreneurs, we become experts at managing risk. We build systems, hire talented people, and create processes that minimize uncertainty. We get good at what we do. Really good. And that's when we become dangerous—to ourselves and our organizations.
When you stop feeling that gut-check sensation of "I might actually fail at this," you stop growing. Your edge dulls. Your hunger fades. You start making safe decisions instead of right decisions.
I've watched too many successful people plateau not because they lacked intelligence or resources, but because they stopped doing things that made their palms sweat. They confused experience with excellence and comfort with competence.
The Biology of Breakthrough
Here's what happens when you commit to something that genuinely scares you: Your entire operating system upgrades. When I signed up for my first Ironman, I didn't just change my training schedule—I revolutionized how I approached everything.
Suddenly, that difficult conversation with an underperforming vendor seemed manageable. After all, I just swam 2.4 miles that morning. The complex real estate deal that had been keeping me up at night? It paled in comparison to facing a 112-mile bike ride in 95-degree heat.
This isn't about minimizing business challenges; it's about expanding your capacity to handle them. When you regularly face voluntary hardship, involuntary hardship loses its sting. Your nervous system adapts. Your threshold for discomfort rises. Your ability to stay calm under pressure becomes automatic rather than forced.
The Transfer Effect
The disciplines required for Ironman training—or rock climbing, or learning to fly, or whatever your scary thing is—transfer directly to business leadership. But not in the ways you might think.
It's not about physical fitness, though that certainly helps with energy and focus. It's about developing what I call "completion capability,” or the ability to finish what you start when every cell in your body wants to quit.
During mile 20 of the marathon portion of an Ironman, after you've already been racing for 10 hours, your mind presents you with a thousand reasonable excuses to stop. You're not injured. You're not failing. You're just uncomfortable. Deeply, profoundly uncomfortable.
Sound familiar? It should. It's the same voice that tells you to postpone the product launch, to avoid the tough personnel decision, to take the safer path with your business strategy.
Choose Your Hard
I'm not saying everyone needs to do an Ironman. I'm saying everyone needs something that makes them question their capabilities. For some, it might be public speaking. For others, it might be learning to tango, writing a book, or doing stand-up comedy.
The specific challenge matters less than its effect on you. It needs to be something where:
Failure is possible and public
Success requires consistent effort over time
You can't buy or delegate your way out
The outcome is uncertain despite your best efforts
Your scary thing isn't about impressing others or posting on social media. It's about reminding yourself that you're capable of more than you think. It's about maintaining the mental flexibility and emotional resilience that made you successful in the first place.
Start Before You're Ready
If you're waiting for the perfect time to take on your scary challenge, you've already failed. There's never a perfect time. You'll always be too busy, too stressed, or too something.
Sign up anyway. Commit publicly. Pay the entry fee. Hire the coach. Book the stage time.
Because here's what I learned standing at that starting line at my last Ironman: The moment you commit to something that scares you, you've already won. Everything after that is just collecting your prize.
What's your Ironman going to be?
When was the last time you committed to doing a “hard” thing? Tell me about the experience in the comments.