Mistakes That Make Us Better

When enthusiasm turns sharp, jokes land wrong, and leadership asks us to listen instead of defend.

There’s a particular kind of mistake that doesn’t come from malice.

It comes from momentum.

From energy.

From wanting to prove yourself capable, strong, valuable.

From caring—just a little too loudly.

Natalie once shared a story with me that still sits heavy, in the best way.

She was early in a season of leadership where she was energized and eager. She wanted to show she could handle it. That she belonged in the room. That she could lead with confidence and decisiveness. One moment of pushing too hard...And in a matter of minutes—just minutes—she damaged a relationship that would take months to rebuild.

No shouting.

No cruelty.

Just intensity without pause.

Conviction without listening.

Strength without softness.

It wasn’t intentional.

But it was real.

That’s the thing about leadership mistakes—they don’t announce themselves as lessons. They show up as moments we wish we could rewind.

When My “Motivation” Became About Me. (I use quotes here because when I wrote this, I noticed a sarcastic judgmental feeling around the word Motivation. Maybe that's a blog for another day)

I have my own version of that story.

Years ago, I had a running joke with a former boss. If my team hit a certain number, I’d get a designer bag—something I’d never normally buy for myself. It was exaggerated. Over the top. A joke.

I even put a picture of it in the office.

I referenced it casually. Playfully.

At least, that’s how it sounded in my head.

What I didn’t hear—until later—was how it landed.

One person on my team finally said it out loud:

That I had made the success of the team about me.

About my reward.

About my win.

It didn’t matter that the bag wasn’t real.

It didn’t matter that it was meant as humor.

What mattered was the message underneath it.

Hit the number so I can get the prize.

There it was.

I.

Me.

Mine.

The team didn’t get a designer bag.

The team didn’t get recognized in that moment.

The spotlight—intentionally or not—was on me.

It was poor judgment.

Bad taste.

And if I’m honest—bad leadership.

I regret the egotism I exhibited. Joke or not.

The Lessons That Didn’t Feel Good at First

That moment taught me things I couldn’t have learned from a book.

First: You don’t win by being right.

I could’ve explained the joke.

Defended the intent.

Clarified what I “meant.”

But leadership isn’t about winning arguments.

It’s about understanding impact.

Second: Be quiet. And listen.

Truly listen—not to respond, not to correct, not to soften the blow—but to hear what someone is brave enough to tell you.

Third—and this one’s harder to admit—

Sometimes the thing you’re most proud of is the thing that gets in the way.

Confidence can turn into noise.

Drive can turn into dominance.

Enthusiasm can turn sharp if it isn’t grounded in awareness.

Damage Isn’t the End of the Story

Natalie rebuilt that relationship. Slowly. Intentionally. With humility instead of urgency.

I rebuilt trust, too.

Not by explaining myself—but by changing how I showed up.

Leadership damage doesn’t disqualify you.

Ignoring it does.

There’s a difference between a mistake that breaks you and a mistake that shapes you. The difference is what you do after.

A Quiet Truth for This Season

If you’re in a tough patch right now—if leadership feels heavier than it used to—hear this:

This hard path is a season.

Not a sentence.

It will come to an end.

You won’t always feel this misunderstood.

You won’t always replay the moment in your head.

You won’t always wonder if you handled it wrong.

But you might always carry the lesson.

And that’s not a burden—that’s wisdom.

A Few Lines to Sit With

The wound became the window,

the silence found its song.

I learned that humble listening

Is where we all belong.

The leader I would one day be

Was formed without applause.

Not by the times I spoke the most

But by the times I paused.

Mistakes don’t make you unfit to lead.

They make you human enough to do it well—if you’re willing to learn.

That’s the work of the Damaged Leader.