I was talking with one of my colleagues last week who was beating himself up over a deal that fell apart. He kept replaying every decision, looking for the fatal mistake, convinced this one failure might define, maybe even sink, his career.
I recognized that spiral immediately. I've been there more times than I can count.
With Thanksgiving around the corner, I've been thinking about failure differently. Because, really, gratitude isn't just about celebrating what went right. It's about recognizing that some of your most important growth came from the moments when everything went sideways.
And that mindset shift changes everything.
My Own 60-Mile Education
Years ago, I signed up for the Keys 100 Ultramarathon specifically because there was a real chance I couldn't finish it. I wanted to test my limits. That’s exactly what I got…plus a masterclass in humility.
I withdrew after 60 miles, completely unprepared for that distance.
That failure still comes to my mind often, even nearing a decade later.
Not because it felt good (it didn't), but because it underlined a lesson I can always stand to be reminded of: preparation beats motivation every single time. You can't willpower your way through inadequate planning, whether you're running 100 miles or scaling a company.
More importantly, that race showed me what happens when you remove the pressure of perfection. I choose not to be devastated by that DNF. Instead, I chose curiosity. What would I do differently? That curiosity has shaped how I approach challenges ever since—in training, in business, in leading teams through difficult seasons.
One failure, properly processed, becomes a reference point you return to again and again.
Why CEOs Should Collect Failures
The executives I respect most all have a mental file of their greatest screw-ups. This might seem like a weird form of professional masochism, but there’s a point to it. It’s now about the sting, but the reflection that comes later.
They don't hide their mistakes or rationalize them away. They study them like Superbowl replays.
There are three reasons this matters:
It makes you approachable. When your team knows you've failed publicly and survived, they stop hiding their mistakes. They bring you problems earlier, when they're still fixable. The culture shifts from "don't screw up" to "learn fast."
It recalibrates your risk tolerance. Every entrepreneur knows you're supposed to take calculated risks. But most of us don't actually calculate—we just hope things work out. When you have a catalog of failures to reference, you start recognizing patterns. You get better at distinguishing between risks worth taking and risks that are just ego in disguise.
It builds genuine resilience. Not the Instagram-quote version of resilience, but the kind that comes from knowing you've been flat on your back before and got up anyway. When the next crisis hits—and it will—you won't catastrophize. You're thinking about what you learned the last time something didn't go as planned.
The Gratitude Connection
This Thanksgiving season, I'm grateful for the deals that fell through, the partnerships that imploded, the launches that flopped. Not in some toxic-positivity way where I pretend they didn't sting or have seriously painful ramifications. They absolutely did.
But I'm grateful because those failures forced me to get better at the fundamentals. They made me a more thoughtful leader. They taught me which battles to fight and which ones to walk away from.
Most of all, they gave me something to offer people beyond advice and capital: I can offer proof that failure isn't fatal. You can make peace with an outcome you didn't want and still build something meaningful from what you learned.
So, Start With One Conversation
If you're leading a team, start your own failure list. Pick three or four that genuinely taught you something, even if the lesson was just "never do that again." Write down what you learned. Then find an opportunity in the next month to share one of those stories with someone who needs to hear it.
Not in a board meeting or company email. Just one person who's struggling with a recent setback and needs to know they're not alone.
Because the best gift you can give as a leader isn't your success story: it's permission to fail forward.
What's a failure that changed how you lead? Share what you learned in the comments.