The Race With Yourself

Sixteen years, one gym, and the opponent that never changes.

About sixteen years ago, I stood in front of maybe thirty people in a gym, a small camera set up behind the baseline, talking about Matt Paul Basketball and the race in front of me. We had just finished a four-day camp. I had just stepped into full-time entrepreneurship—no safety net, no script—only belief and momentum.

That week, I had been leaning on a phrase I kept repeating to myself, hoping it was true:

The race is with yourself.

At some point during camp, one of the kids—Connor Lyons—said it back to me.

Not to echo me.

Not to impress anyone.

Just plainly. Almost like a reminder.

I even remember the feedback I received from one of the parents that week. He told me something simple—something I still think about to this day: ask more questions.

Connor listened that week. The way kids do when they aren’t trying to argue with an idea, just hold onto it. He must be a college graduate by now. Maybe more. Life has likely added weight to that sentence since the day he handed it back to me.

I thought about Connor this morning as I walked into the gym on a frigid seven-degree day. The kind of cold that sharpens everything—your breath, your focus, your purpose.

In the middle of the room, a heavy bag hung from the ceiling, swaying slightly. An old teammate. An old classmate from Chestnut Hill Academy. Two oversized black boxing gloves. A steady rhythm. Thud after thud.

I asked him who he was boxing.

“Myself,” he said.

He told me he’s about to retire from the police force. Twenty-five years. He’s earned the right to stop—to do nothing if he wants.

And yet, there he was. Still punching. Still moving.

It reminded me of something Tommy Whitworth once shared with me about basketball and player roles. Run your race. Not someone else’s. Not the loudest one. Every player has a role. Do your job. Stay connected. Run your race with purpose and trust that the team needs exactly that from you.

It struck me then that the entrepreneurial race—the one I started sixteen years ago—is long and winding. It doesn’t end with a finish line so much as it bends into new terrain. Sometimes it’s exhilarating. Sometimes lonely. Sometimes cold.

Watching him, I smiled. And I felt something else too—for a man finishing one race and quietly choosing another.

Because the race was never against the clock.

Or the competition.

Or the career.

It’s with yourself.