What Do You Do When You Mess Up?
Last week, something went sideways during one of my biggest workshops. Here’s what happened — and what it teaches you and me.
This Week’s Courage Newsletter
“The glitch was the teacher.” — me
Why our most painful missteps can become the moments that shape us most
This Week's Scare Your Soul Challenge: Find the Lesson in the Glitch
Bottom line: You don’t grow by avoiding mistakes. You grow by owning them — and letting them refine you.
Dear Courageous Souls (and Honest Reflectors),
If I’m being honest — and I want to be —
I’d love to sit here and tell you how amazing everything is going.
That my professional life is all momentum and magic.
That I just led eight workshops for a large client — and they were flawless.
That I’m checking every box, making an impact, and feeling totally aligned.
But that wouldn’t be the whole story.
And it wouldn’t be true to the work I ask all of us to do.
So here’s the truth:
Yes, I led eight workshops for an NBA franchise last week.
It was meaningful, challenging, beautiful. The largest number I’ve ever done for a single client.
Two workshops a day. Four days.
A marathon of creativity, emotion, connection, and intensity.
And yes — most of them went wonderfully.
But one moment went sideways.
And it cracked something open in me.
The Glitch
In one of the sessions, I led an exercise I’ve done dozens of times — one that asks each person to share a personal purpose statement about their work, and then invite others to walk around the room and leave affirmations of what they see in those words.
It’s a sacred part of the workshop. A moment of being deeply seen.
But this time, something happened that I’ve never seen before:
One person was unintentionally left out.
No one wrote affirmations on her statement.
She had written something honest and powerful — and it went unseen.
She sat quietly as others received words of affirmation… and hers sat untouched.
She was emotional. Rightfully so.
And I felt terrible. Deeply responsible. Sick to my stomach.
I had failed — not in intention, but in execution.
Obviously, we all run into moments of failure, of mistakes, and I really believe that it is how we deal with them, not whether we make them, that we truly become courageous.
Failure is inevitable if we are pushing and growing.
And so I chose a path.
Here’s what I chose to do:
🟡 I sat with her afterward. I listened. I apologized. I validated her words.
🟡 That night, I wrote her a heartfelt email. Not a Band-Aid. Not a fix. But a reflection. I shared what her words meant to me, how they moved me, how they revealed a kind of quiet leadership I deeply admire.
🟡 Two days later, she wrote me back. Her response was gracious, emotional, and generous. She not only accepted my words — she shared what the workshop opened up for her. She linked her reflection back to a prior role that had once lit her up. And she thanked me.
The Real Work
That moment became the defining moment of the week.
Not the applause. Not the high-fives.
But the glitch.
That’s where the work lives.
Failure is inevitable when you’re stretching.
Mistakes are part of the terrain when you’re leading anything real.
The question isn’t if you’ll fail.
It’s who you’ll become when it happens.
So I got curious.
I reached out to trusted colleagues. I asked: How could I make sure this never happens again?
Then I made a shift in my process. I changed how I guide that part of the workshop — and honestly?
I think it’s now even better.
And in a strange way, I feel proud of that.
Not because I failed — but because I faced it.
Even writing this is hard.
Part of me still wants to lead with the polished version — to tell you how great it all went.
But the glitch?
The glitch is the teacher.
This Week's Scare Your Soul Challenge: Find the Lesson in the Glitch
Notice the moment this week that doesn’t go as planned.
(It’ll come. They always do.)Pause. Feel what you feel. Don’t rush past it.
Take ownership — even if it wasn’t all your fault.
Ask: What can I learn? What can I change? What kind of leader/human/friend do I want to be in this moment?Ask for insight. Don’t isolate in shame.
Make it better. Even just a little.
That’s where courage lives.
In the glitch.
In the gut-check.
In the willingness to grow in real time.
You don’t need to be perfect.
You just need to stay awake — and brave.
With imperfection, honesty, and a still-beating heart,
