What a Rollerblading Class Taught Me About Risk

One New Year’s Eve, I took stock and realized that it had been a great year, but I was drained.

Because I had taken on a lot—and was addicted to doing them all well. I sought A’s across the board.

If I was being honest, I had made those A’s the markers of my self-worth. And never risked questioning that equation.

But the pattern wasn’t satisfying or sustainable, so my only resolution that New Year was to try 3 things that were:

New to me.
Completely outside my realm of competence and aptitude.
Where an A was impossible unless it was for effort.

I was giving myself permission to fail and see what happened. Would I fall apart? Learn to chill?

My first pick was a rollerblading class. It checked both boxes:

1. No experience (I expected a blade, not wheels).
2. Low aptitude: I couldn’t skate or ride a bike. My balance sucked.

The morning of class: Every other adult was a parent. Every other student was under 10.

The instructor handed out helmets, wrist guards, elbow and kneepads, and rollerblades. Though intimidated, I felt legit, like I was in a Nike ad.

The kids stood up. Some leaned on a parent. Others sprang up as if born on wheels.

I grabbed a post and pulled myself up. So far so good. Then I let go.

Boom! I’m on my butt.

Embarrassed but uninjured, I glanced around. No one was looking.

I grabbed the post again. Stood up. Let go. Fell.

That was my entire class. Stand. Let go. Fall. Stand. Let go. Fall.

Meanwhile, the kids whizzed by, whooping and turning.

I stayed till the end but ran away as soon as I could, with a bruised butt (and ego).

Looking back: Though I didn’t learn to rollerblade, I did get what I came for:

My lack of skill relieved me of the pressure to perform.
It dented my stories about perfectionism and self-worth.

This was a big deal for me.

Psychological Safety—the belief you can raise doubts, make mistakes, and try new things without shame or ridicule—is the #1 driver of exceptional team performance.

If you’re a people leader, here’s a challenge for you:

Between Monday and Friday next week, tell your team about one risk you took that didn’t play out the way you hoped. Or one consequential mistake that you’ve tried to learn from.

Trust me when I tell you that you aren’t lowering the bar; you’re modeling it’s ok to try new things (innovate) and take accountability (raise a flag or admit a mistake).

What’s a new thing you tried (and survived to tell the tale)?

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