I Thought I’d Be Further Along by Now

15 years of entrepreneurship taught me something I never expected about success.

When I started my first business at 23 years old, I had some pretty big dreams.

I pictured myself standing on stages, speaking to rooms packed with people. I’d write a few books, become a recognized expert in my field, and build a reputation that extended far beyond my local community.

I could see it all so clearly.

And I genuinely believed that if I just worked hard enough, stayed committed, and refused to give up, eventually I’d get there.

After all, isn’t that what we were taught?

I grew up in the ’90s, when movies like The Mighty Ducks and Little Giants taught us that the underdogs always win if they just believe in themselves and work hard enough.

The main character has a dream. They face obstacles. People doubt them. They work harder, refuse to quit, and eventually, against all odds, they get exactly what they wanted.

I loved those stories. I still do.

But 15 years into entrepreneurship, I’ve discovered that real life doesn’t always follow a Hollywood script.

Sometimes you do everything right and still don’t win the championship.

Sometimes you work incredibly hard, make sacrifices, invest in yourself, and show up day after day, only to find that the future looks nothing like the one you imagined.

And that’s a difficult thing to come to terms with.

Especially when you’re someone who has always believed that hard work and determination could make just about anything possible.

The Problem With Chasing a Dream

For a long time, I measured my success against that picture I’d created when I was 23.

And when I looked at where I was compared to where I thought I’d be, it was easy to feel like I was falling short.

Never mind the businesses I’d built, the people I’d helped, the challenges I’d overcome, or the countless lessons I’d learned.

There was always that nagging feeling that I should be further along.

Recently, though, something shifted.

I started thinking about that 23-year-old girl who believed the entire world was her oyster.

And I asked myself a different question.

Would she be proud of the woman I’ve become?

I sat with that for a moment.

And the answer was an overwhelming yes.

She’d be proud of the courage it took to start. The businesses I’ve built. The people I’ve helped. The mistakes I’ve recovered from. The resilience I’ve developed.

She’d be amazed by the things I’ve learned, the difficult situations I’ve navigated, and the woman I’ve become through it all.

And I realized something.

I’d been so busy measuring the distance between where I was and where I thought I’d be that I’d forgotten to appreciate how far I’d actually come.

Maybe the Dream Was Never the Whole Point

Remember Cool Runnings?

The Jamaican bobsled team worked incredibly hard to make it to the Olympics. They trained, sacrificed, and overcame impossible odds.

And in the end, they didn’t win the gold medal.

They didn’t even finish the race.

But they picked up their sled, carried it across the finish line, and walked away with something arguably more valuable than a medal.

Pride. Character. Friendship. And the knowledge that they’d accomplished something extraordinary.

I think there’s a lesson in that for all of us.

We can become so attached to a particular outcome that we completely overlook the value of the journey.

And sometimes, what we gain along the way turns out to be far more meaningful than what we originally set out to achieve.

I’ve been learning to hold my dreams with open hands.

To keep imagining, creating, and pursuing meaningful things, but to stop believing that success has to look exactly the way I pictured it.

Because maybe the life that unfolds isn’t the one we imagined.

Maybe it’s actually the one we need.

Give Yourself Some Credit

As we approach Thanksgiving, I want to encourage you to do something.

Before you start thinking about everything you still want to accomplish, take a moment to look backward.

Think about the person you were when you started your business.

What did you know then? What were you afraid of? What challenges have you overcome that once seemed impossible?

Think about the people you’ve helped, the lessons you’ve learned, and the person you’ve become.

And ask yourself:

Would the younger version of me be proud of who I am today?

I hope the answer is yes.

Not because you’ve accomplished everything you imagined, but because you’ve grown in ways you never could have anticipated.

You don’t owe your younger self the exact future they imagined. But you do owe yourself the opportunity to appreciate the person you’ve become.

And maybe that’s something worth being thankful for.