Michael was 32, running his own company, and convinced he was behind.
Behind where he should be. Behind where he thought other founders were. Behind some imaginary version of himself that had it more figured out.
On the first day of our two-day retreat I asked him to write down all the ways he was hard on himself.
It was quite a list.
We spent time talking about his life, his company, and what he actually wanted. Not the pitch version. The real version.
At some point on day two, I suggested we take a walk. There’s a famous record shop a little more than a mile from the hotel (the Limelight in downtown Denver).
I’ve learned that the less agenda I bring into these two days, the more the space does the work — for both of us. The walk wasn’t a technique. It just felt like the right next thing.
Wax Trax Records is Denver’s oldest record shop, packed floor to ceiling with vinyl, turntables, the smell of old cardboard and carpet remnants. There’s a second store next door just for used LPs. We wandered around for a while and I bought some classic jazz LPs. Davis, Coltrane, Monk, Rollins.
On the walk back, Michael looked at me.
“I’ve realized a couple things.”
“What’s that?”
“First — I’m way too hard on myself.”
“And?”
He paused.
“I’m thinking way too small.”
That combination stopped me. Those two things almost never arrive together. Most founders, if they soften the self-criticism, they relax. If they stay ambitious, they stay brutal with themselves. Michael had found both exits at the same time.
He didn’t get there because we solved a problem or cracked a framework. He got there because for two days, the pressure was off. He could finally see himself clearly. And when you see clearly, the next step is usually obvious.
A few weeks later he sent me a note. Part of it said:
“I’m not just delegating — I’m empowering. I had a meeting with my marketing director, and instead of jumping in with my own ideas, I asked, ‘Where’s your head at?’ That small shift changed everything.”
One moment on a walk.
That’s what a little space can make possible.
An Opportunity for Deeper Work
I’m opening a small group this June for founders ready for this kind of work. Twelve people. A full year. If something in this story landed for you, it might be worth a look.
More details in this HERE