I’ve Never Seen the Bears Win - And I Still Believe

Let’s get one thing straight:
I’ve never seen the Bears win a Super Bowl in my lifetime.

And yet, I still watch every single press conference.
Rewatch every game like I’m studying film.
Live and die with every 3rd down stop and every busted screen pass.
Because for me—and for millions of us—this team means more than trophies.

In Chapter 12 of Punching Above Your Weight, I wrote a section called:

Underdog Interlude – The Bears Have Always Been Built for the Long Game

It’s about Devin Hester.
But really, it’s about Chicago itself.

“That was for Chicago.”
- Devin Hester, postgame, Super Bowl XLI

Everyone in the world knew what was coming.
Hester still found the seam.
And for a fleeting second, we weren’t just watching history—we were part of it.

That return didn’t win us the trophy.
But it did something just as powerful:

It reminded the world what Chicago is made of.
Resilience. Rhythm.
Grit that doesn’t flinch in the spotlight.

I included this story in the final round of the book for a reason.

Because punching above your weight isn’t about a perfect record.
It’s about how you keep showing up when the world thinks you're done.

And the Bears—like this city—always show up.

I don’t just watch the Bears.
I study them.

Because in a world obsessed with quick wins, the Bears remind me that the long game still matters.
That culture is built one tough decision, one gut-check play, one unseen rep at a time.

And I carry that mindset into everything I build—whether it’s a book, a product, or a team.
Not because the spotlight is on.
But because I know how to fight in the dark.

This one’s for Chicago.
And if you know, you know.

—

📖 Punching Above Your Weight is available now.
But if you only read one page, make it this one—because I wrote it with everything I had.