Choose Your Hard: Lessons from Finishing Dead Last at the JFK 50
Lessons From the JFK 50
Four years. Four attempts. One goal: finish the JFK 50, America's oldest ultra-marathon.
This year, I finally did it—but not the way you might expect. I crossed the finish line with just three minutes to spare, coming in dead last. And you know what? I’m thrilled.
This experience wasn’t about beating other runners or setting records. It was about agency—the power to choose my hard before life chooses it for me. And that’s a lesson I think we all need to hear.
The Backstory of the JFK 50
The JFK 50 began as a fitness initiative in the 1960s under President John F. Kennedy. Concerned about the nation's declining physical health, JFK challenged Americans to embrace fitness as a lifestyle, not just an afterthought.
The 50-mile ultra-marathon has evolved over six decades, welcoming runners of all abilities, from elite athletes to everyday folks like me. It’s known for its brutal terrain, relentless time cutoffs, and the sense of accomplishment that comes with finishing.
I learned about the race four years ago and felt an immediate pull. Could I push myself to complete something this hard? I didn’t know, but I was willing to try.
Three Failures, One Finish
The first three attempts were tough. I didn’t finish. Each year, I stopped short of the goal:
Year 1: Mile 42
Year 2: Mile 38
Year 3: Pulled off the course for missing a cutoff
This year, everything changed. After countless training runs and recovering from a knee injury just 80 days before the race, I crossed the finish line. The clock read 12 hours, 57 minutes, and 18 seconds.
Lessons from Coming in Last
It’s easy to think of finishing last as failure, but here’s what I learned:
You Choose Your Hard, or Life Chooses It for You
Life is full of challenges. You can either face them head-on by choosing hard things intentionally, or you can let life throw them at you unprepared. When you choose your hard—whether it’s running 50 miles, tackling a difficult conversation, or building a business—you grow stronger for whatever comes next.Health is the Foundation of Freedom
JFK’s call for physical fitness wasn’t just about looking good; it was about preserving freedom. A clear mind and strong body enable you to show up for your family, your business, and yourself. Ignoring your health isn’t neutral—it’s actively destructive.Success is Finishing, Not Winning
My time was nowhere near the record set this year by David Sinclair, who finished in just over 5 hours. But success isn’t about comparing yourself to others. It’s about setting a goal, showing up, and finishing.Every Finish Line is a Starting Point
Crossing that finish line wasn’t the end—it was a reminder to keep moving forward. Whether you’re running, growing your business, or just trying to make it through a tough season, every milestone is a launchpad for the next goal.
A Simple Practice to Appreciate Life
I want to share a practice I’ve learned, called the “Last Time Exercise.” The idea is simple: what if this moment were the last time you ever experienced it?
The last time you pick up your child.
The last time you share a meal with a loved one.
The last time you go for a run.
You don’t need to change your actions—just your perspective. It’s not about dwelling on loss, but savoring the moment.
What Will You Choose?
Finishing the JFK 50 taught me this: hard things are worth doing. They build resilience, confidence, and a sense of agency over your life.
So, what hard thing will you choose? A healthier lifestyle? Tough decisions in your business? A goal that feels just out of reach?
Remember, if you don’t choose your hard, life will choose it for you.
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Final Thought: Success is Never Final
Winston Churchill once said, “Success is not final, failure is not fatal: it is the courage to continue that counts.”
Dead last, but I finished. And I couldn’t be more grateful for the journey.
What’s your next hard thing?