Being a Chicago sports fan made me tougher

It's been a while since I've written to you.

I was sitting here at the pool at my apartment complex in the Gulch when it hit me – I've been slacking on these emails.

The sun's hitting just right, there's some grown ass men doing cannon balls even though the sign clearly says "NO DIVING," and I'm watching highlights from yesterday's games.

NFL season just started.

And if you know anything about me, you know I'm a Chicago sports fan.

Which means I'm basically a professional masochist.

If you keep up with Chicago sports, you'll understand the pain.

The Bulls? Mediocre for over a decade.

The Bears? Ben Johnson can’t even save this team.

The Blackhawks? They had their moment, but that was years ago.

The only "decent" team is the Cubs, but here's the thing...

I'm a White Sox fan.

So even when Chicago has something good going, it just doesn't hit the same.

Most of the time, watching these teams is pure suffering.

You get your hopes up, think "maybe this is the year," and then boom.

Disappointment.

Every. Single. Time.

But here's the weird part...

Every once in a while, something magical happens.

The Sox make the playoffs.

The Bears have one of those games where they score more than 14 points in a half.

The Bulls hit a game winning three against the Lakers.

And in that moment?

All the pain, all the losses, all the years of disappointment...

It's worth it.

That one win makes you forget about everything else.

Business is the exact same way.

Right now, you might be taking loss after loss.

Your cold emails are getting ignored.

Your content isn't hitting.

You're watching everyone else succeed while you're stuck spinning your wheels.

Some nights you're probably wondering if this whole entrepreneur thing is just a delusion.

Maybe you should just go back to your 9-to-5 and accept the cubicle life.

But here's what being a Chicago sports fan taught me...

You only need one win to change everything.

One client says yes.

One post goes viral.

One opportunity opens up.

And suddenly, all those losses weren't losses – they were training.

Every "no" you got was preparing you for the "yes" that changes your life.

Every failed attempt was building the calluses you need to handle success.

Just like how all those years of Chicago sports heartbreak made that one good season feel like pure ecstasy...

All these business failures are setting you up for a win that'll feel better than anything you can imagine.

The difference between winners and losers isn't talent.

It's who can take more punches and keep getting back up.

Chicago sports fans are built different.

We know how to suffer.

We know how to hope when there's no logical reason to hope.

And when we finally win?

We appreciate it more than anyone else could.

So keep taking your swings.

Keep getting back up.

Keep believing in something that might seem impossible.

Because when that win finally comes – and it will come – you'll understand why every single loss was worth it.

Now if you'll excuse me, I need to go convince myself the Bears might actually be good this year.

(They won't be, but that's beside the point.)

To delusional optimism,

Grant