Field Notes · No. 08

I’ve Never Seen the Bears Win, and I Still Believe

I watch every press conference. I rewatch every game like I’m breaking down film.

The book held open to the Underdog Interlude about the Bears, against a window overlooking downtown buildings

I’ll get this out of the way: the Bears have not won a Super Bowl in my lifetime.

I watch every press conference anyway. I rewatch games the way a coach breaks down film. I live and die with every third-down stop and every screen pass that falls apart. For me, and for a few million other people in this city, the team means more than its trophy case.

Chapter 12 of Punching Above Your Weight has a short section called “Underdog Interlude: The Bears Have Always Been Built for the Long Game.” On the surface it’s about Devin Hester. Underneath, it’s about Chicago.

“This is what I had been envisioning all week and actually for the past two weeks. We had the chance to come out with the kickoff return on the first play of the game. But the bad part about it is that we didn’t come out with the victory.”

Devin Hester, after Super Bowl XLI

Everybody watching knew what was coming, and Hester found the seam anyway. Ninety-two yards. Nobody had ever returned the opening kickoff of a Super Bowl for a score. For a few seconds we weren’t watching history so much as standing inside it.

That return didn’t win us the trophy. It did something I’ve come to think matters just as much. It reminded the world what Chicago is made of: resilience, rhythm, and the kind of grit that doesn’t flinch when the lights come on.

I put that story in the final round of the book on purpose. Punching above your weight was never about a perfect record. It’s about how you keep showing up after the world has decided you’re finished, and the Bears, like this city, keep showing up.

So I don’t just watch them. I study them. In a culture that wants everything to pay off by Friday, they’re a weekly reminder that the long game still matters, and that a culture gets built one hard decision, one gut-check play, one rep nobody sees at a time.

I try to carry that into everything I build, whether it’s a book, a product, or a team. I don’t do it for the spotlight. I do it because I know how to fight in the dark.

This one’s for Chicago. If you know, you know.

Punching Above Your Weight is out now. If you only read one page of it, make it this one. I wrote it with everything I had.