The Slow Burn: The chips are stacked

It's one thing to say you're going to do something.

It's another thing entirely to commit.

I've been thinking a lot about that lately.

Last week, I wrote about finding myself in a Robert Frost situation. Two roads diverging in the woods. One path was familiar. Predictable. Safe. The other required a little faith.

To expedite the metaphor, the road less traveled for me is carving my own path.

(IYKYK. Thanks, Jon Huber.)

A few weeks ago, I got offered a role with an organization I genuinely admire. Not one of those opportunities you immediately dismiss. Quite the opposite.

The compensation was exceptional.

The people were exceptional.

The mission was compelling.

On paper, it was the kind of opportunity most people spend years trying to find.

So I did what I've learned to do when life puts something significant in front of me.

I played the tape.

Not the first inning.

Not the first quarter.

The whole tape.

I tried to imagine what life would look like a few years down the road.

At first, it looked pretty awesome.

The signing bonus alone had me mentally building out a humidor full of Atabeys, Byrons, Behikes, and Padron Blacks. I had already started spending money that wasn't mine.

You know...responsible adult behavior.

But once the novelty wore off, I started asking deeper questions.

What would our life actually look like?

Would we have more money?

Absolutely.

Would we have more security?

Probably.

Would we have a clearer path?

Without question.

But something kept bothering me.

I couldn't shake the feeling that while life would have been good, it wouldn't have been ours.

At least not completely.

I've realized something over the last few years.

I don't really care about winning somebody else's game.

Even if it's a really good game.

Even if the rewards are substantial.

Even if everyone around me tells me it's the smart move.

Because somewhere deep down, I know how I'm wired.

Kaitlyn knows it too.

We're builders.

We're encouragers.

We're the type of people who see something that doesn't exist and immediately start discussing how to make it real.

It's both our greatest strength and our greatest character defect.

Most sane people would probably choose stability.

Meanwhile, we're over here trying to build a cigar company from scratch.

So naturally, we chose chaos.

The more I played the tape forward, the more one question kept showing up.

What if we never fully believed in ourselves?

Not what if we failed.

What if we never tried?

That question hit harder than any financial projection ever could.

Because I've met people who failed.

I've been one of them.

Failure is survivable.

Regret is a different animal.

Regret sits with you.

It follows you around.

It shows up years later when you're driving home alone or sitting on a porch somewhere watching the sun go down.

It whispers questions that don't have answers.

What if?

What could have happened?

What would life have looked like if I'd just been a little braver?

And maybe that's why this week, despite being a complete dumpster fire, has strangely felt like confirmation.

The dumpster fire?

Boxes.

Just boxes.

We've spent the better part of a year designing elements of Brolo around a specific box format.

Dimensions.

Presentation.

User experience.

Design.

Branding.

All of it.

Then this week we got told that box is no longer an option.

Just like that.

Gone.

No backup plan.

No one riding in on a white horse to save the day.

No magical cigar fairy fixing the problem overnight.

Just us.

Back to the drawing board.

One thing I've learned about the cigar industry is that every box manufacturer appears to be called "Cigar Box Factory."

I'm not exaggerating.

The only way to know which company you're talking to is by knowing the manager's first name.

Most of them don't speak English.

I don't speak Spanish.

So we've all been united by confusion.

It's been beautiful.

And mildly infuriating.

But honestly?

These are the problems I want.

I'd rather spend my day trying to solve problems connected to a dream than spend my day solving problems connected to a paycheck.

Not because paychecks are bad.

They're not.

They've fed my family.

They've paid mortgages.

They've carried us through seasons where dreams alone wouldn't have.

But eventually there comes a moment where you have to decide whether you're building someone else's vision or your own.

This was one of those moments.

So we pushed the chips in.

Again.

Not because it's guaranteed.

Not because we're fearless.

Not because we have some secret knowledge that everything will work out.

Quite the opposite.

We're doing it knowing it might not.

Knowing there will be setbacks.

Knowing there will be long nights.

Knowing there will be moments where we question whether we're qualified for any of this.

But we're doing it anyway.

Because if there's one thing I've learned, courage isn't certainty.

Courage is moving forward despite uncertainty.

So if you're reading this and you've been sitting on an idea...

Take the chance.

Ask the girl.

Raise the funding.

Write the book.

Launch the product.

Start the company.

Apply for the job.

Have the conversation.

Do the thing.

Because if you don't, someone else will.

And you'll find yourself becoming Uncle Rico.

Standing in the middle of nowhere, talking about how Coach should have put you in during the fourth quarter.

Convinced you could have thrown that football over those mountains.

Maybe you could have.

Maybe you couldn't have.

But you'll never know.

And that's the tragedy.

The older I get, the more I realize growing up isn't learning what opportunities to say yes to.

It's learning what opportunities to say no to.

Sometimes saying no to something good creates room for something greater.

And sometimes the biggest gamble isn't betting on yourself.

The biggest gamble is spending your entire life wondering if you should have.

So here's to the dreamers.

The builders.

The entrepreneurs.

The artists.

The weirdos.

The people creating things nobody asked them to create.

The people taking a shot when there are easier options available.

Push the chips in.

You might lose.

You might win.

But at least you'll know how the story ends.