The Kids I Failed—And What They Taught Me About Love

I’m not a big fan of letting regret shape my life.

That said, God knows I’ve made enough mistakes to fill a Major League Baseball stadium a few times over.

The other day, I drove past a youth baseball field and found myself flooded by memories.
I spent years coaching baseball—rec leagues, travel teams, even five seasons at the high school level.
I took pride in it, too: helping boys grow into strong, confident young men.
At least, I thought I had done it right.

But a few days ago, I stumbled across the LinkedIn profile of one of my former players.
I barely recognized him—no longer the awkward little kid who rode the bench, but a strong, capable young man trying to find his way in the world.

And suddenly, a light turned on inside me.
A painful, necessary light.

I realized:
I had been a dynamic coach for the best players—the naturals, the kids who always made the lineup.
They loved me. I loved them. It was easy.

But what about the ones who batted eighth or ninth?
The ones who sat, waiting, hoping for a chance that rarely came?

Full confession:
I failed those kids.

Those who needed the most... got the least.
Kids placed in my care found confirmation of what they already feared:
they weren't quite good enough.
I reinforced it—not intentionally, but undeniably.

And now I live with that regret.

One kid battled family divorce.
Another carried the heavy, invisible ache of a seriously ill sibling.
One of them, struggling in ways I failed to see, eventually took his own life.
He wore my team's jersey.
I wore the blinders.

I should have known.
I should have seen.
But I was too focused on the wins, the standings, the scoreboard.

Rascal Flatts has a song called "Why" that haunts me still.
There's a line:

"Was there anything I could have said or done?
Had no clue you were masking a troubled soul."

Every kid has a story.
Even the ones who shine.
Especially the ones who don’t.

I missed too many chances to speak life into kids who didn’t have a trophy to show for their courage.
And somehow, it took me a decade to realize the real scoreboard I should have been playing for.

Today, I lead people in corporate America.
Some are top performers.
Some are struggling.
It’s easy to pour energy into the stars—the ones who shine bright and make me look good.

But I’m learning:
real leadership happens at the bottom of the leaderboard.

It happens in the quiet, unseen moments—
in listening without rushing,
in believing without proof,
in standing beside the ones who aren’t easy to stand beside.

Not because they’re "projects" to be fixed.
But because they’re human beings, sacred and worth fighting for, exactly where they are.

There’s an old saying:

“We’re all just walking each other home.”

Even the ones trailing in the back of the crowd.
Especially the ones trailing in the back of the crowd.

Never give up on people.
Never leave anyone behind.
No exceptions.

Author’s Note

In December of this past year, I was released from my corporate role.
Not with malice—but with metrics.
Not with cruelty—but with coldness.
By the numbers, I wasn’t “worth saving.”

It’s a strange, sobering thing to find yourself on the other side of the scoreboard.
To realize how easy it is to overlook the sacredness of a person when all you measure is performance.

I share this because the story I wrote above isn’t just a reflection on the past.
It’s a mirror I now carry into my future.

Today, I know with deeper clarity:
Every soul matters.
Every story deserves attention.
Every person deserves to be seen beyond their statistics.

Including you.
Including me.

Especially on the days when we feel left behind.