What Staring Down Fifty Taught Me About Success, Failure, and the Wrong Scoreboard

I want to tell you a story.

I want to tell you the story of a failure.

This man failed two out of every three times he tried.

Read that again.

Two out of every three.

Nineteen seasons as a Major League Baseball player, and in roughly 66% percent of his trips to the plate, he failed.

By just about any standard, that’s a spectacular failure rate.

Except…

He never once finished a season batting under .300.

He collected more than 3,100 hits.

He won eight batting titles.

He became a first-ballot Hall of Famer.

His name was Tony Gwynn.

In my humble opinion, Tony Gwynn was the greatest pure hitter I’ve ever seen. Granted, I’m too young to have seen Ted Williams or Hank Aaron, but I’ve never seen anyone do with a baseball what Tony Gwynn could.

Simply put, he was a surgeon with a bat in his hands.

There was a playoff game where Gwynn’s Padres faced the Astros’ Randy Johnson—another Hall of Famer. Johnson threw a pitch that was nearly a foot off the plate. Most hitters would’ve watched it sail harmlessly into the catcher’s mitt for a ball.

Gwynn somehow reached it, barreled it up, and lined it down the left-field line for a double.

It’s still one of the most ridiculous pieces of hitting I’ve ever seen.

Yet two out of every three times he stepped into the batter’s box…he failed.

Funny how perspective changes everything.

It amazes me how many people we think of as wildly successful spent enormous portions of their lives failing.

James Dyson went through more than five thousand prototypes before building the vacuum cleaner that made him a household name.

Spanx founder Sara Blakely’s father used to ask his kids at the dinner table, “What did you fail at today?” If they didn’t have an answer, he was disappointed. Disappointed not because they had failed, but because they hadn’t tried anything difficult enough to fail.

Walt Disney was fired from a newspaper for “lacking imagination.”

I repeat, Walt Disney was fired for lacking imagination.

That’s a sentence that exists…

History is full of spectacular failures.

So why are so many of us terrified of becoming one?

Here’s why this has been rattling around in my head and on my heart lately.

Next March, I turn fifty.

And if I’m being honest, that number has scared me more than I’d like to admit.

When I was ten years old, I had a very different picture of what fifty looked like.

I imagined a wedding ring.

A family.

A career that was firmly established.

Financial security.

Confidence.

Stability.

The funny thing about childhood is that it assumes adults eventually stop wondering if they’re enough.

Instead, I’m writing this on my first day off in ten days from my retail job that pays the bills while I chase the dream that’s been following me my entire life.

I’ve written and published books.

Hosted podcasts.

Interviewed people I’ve admired for years.

I’m about to publish my fifth novel.

And yet there are still mornings when I look in the mirror and wonder if I somehow took a wrong turn.

A customer at work asked me a question the other day that I haven’t been able to shake.

We’d developed a good rapport while she was shopping. We started talking about creative work—she was also in a creative field. I mentioned that I was an author and that my fifth novel was coming out later this year.

She stopped.

Looked me dead in the eye and asked me a question that rattled me to my soul.

“Why are you still here?”

Yeah…

On the outside, I laughed.

Kinda.

I gave her the practical answer from a man still hoping to close a deal.

“I still need to pay rent.”

But it wasn’t the truth.

The truth was much harder to admit.

Because I don’t know that I’ve believed in myself deeply enough to bet on myself.

Not talent.

Not ideas.

Not work ethic.

Belief.

The kind of almost irrational belief that keeps someone building more than five thousand prototypes.

The kind of belief that keeps walking back to the batter’s box after making an out with runners on base.

Honestly, I think I’ve spent a lot of time looking at my life through the wrong scoreboard.

I see the relationships that never bloomed.

The career that hasn’t fully arrived.

The opportunities I missed.

The years I feel like I wasted.

But when I force myself to zoom out, I see something else.

I see someone who’s fought like hell to climb out of some pretty dark places.

Someone who’s written books that didn’t exist fifteen years ago.

Someone who’s built friendships that have changed his life.

Someone readers believe in, even when he struggles to believe in himself.

Someone who’s still standing.

That’s not failure.

That’s just a game that’s still being played.

One of my greatest creative heroes is Aaron Sorkin.

Years ago, he created and wrote a short-lived television series called Sports Night. In one episode, a businessman explains the philosophy behind his company.

And that philosophy has shaken me to my core for more than 25 years.

“I’m what the world considers to be a phenomenally successful man, and I’ve failed much more than I’ve succeeded. Every time I fail, I get my people together and I say, ‘Where are we going?'”

The name of his company was Quo Vadimus.

It means:

“Where are we going?”

Sorkin’s confounding fascination with Latin aside, I wonder if that’s the better question.

Not:

“Why am I not where I thought I’d be?”

Not:

“Why am I still here?”

But…

“Where are we going?”

Hank Aaron’s personal motto was simple:

“Just keep swinging.”