Start Over. Look Stupid. Keep Going.
When the thing that once defined you stops working.
There’s a moment—if you’re lucky—where the thing that used to define you stops working.
Not because it failed.
Because it’s over.
But instead of walking away clean, most of us drag it behind us like a busted suitcase. Still trying to prove we’re that guy. Still looking for someone to validate a version of ourselves we quietly outgrew years ago.
Why? Because starting fresh feels like failure. Especially in midlife.
When you're younger, reinvention is sexy. It’s brave. People root for you.
When you're older, it feels like a demotion.
In Season 2: Ep 1 of Man in the Middle, Joe and I talked about what it takes to drop the old identity and begin again—even when your pride’s screaming for you to stay put.
Joe told a story about prepping for his first triathlon. He used to be a competitive bodybuilder—jacked, intense, commanding. He walked into every room like a man who’d already earned the spotlight.
But endurance sports don’t care how many plates you can bench.
They require a different kind of strength.
So Joe shaved off his hair, his beard, and God knows what else. Not just for speed. For clarity. For a clean break.
He walked into the gym—a place where he used to dominate—and started over as the most awkward guy in the pool.
No applause. No respect. Just him, alone with his choice.
That’s the moment most people avoid.
The beginner’s moment. When your ego’s too loud, your skill’s too low, and your past achievements don’t mean a damn thing to the thing in front of you.
I’ve been there.
Letting go of who I thought I was. Sitting in silence. No crowd. No “next step” to post about. Just me, the work, and the question: What now?
Most days, I didn’t have an answer. But I had a broom.
And the guy with the best broom? He’s the one who sweeps the most.
There’s no shortcut. No hack. Just showing up again and again until the new version of you shows up too.
If you’re feeling that nudge right now—like something inside you is done pretending, done performing, done clinging—listen to it.
Start over. Look stupid. Keep going.
—Kevin