What Risking Failure Taught Me in Baghdad
Years ago, I led a night search-and-seizure mission in Baghdad.
We were targeting a sniper—a dangerous and effective one who had taken the lives of several of our fellow soldiers. The mission was critical. If we succeeded, we’d save lives. But the risks were high, and the possibility of failure was real. We didn’t know if the intel was a trap. We didn’t know if we’d all make it home.
But we went.
We executed. We detained the sniper. And no one on my team was injured.
Looking back, it’s one of my proudest moments—not because of the outcome, but because of the willingness to lean into the possibility of failure for the chance to do something truly important.
That’s the leadership lesson.
In Never Play It Safe, author Chase Jarvis outlines five rules for failing that every steady leader should know:
Don’t fail before you fail – Don’t veto yourself. The world will give you enough obstacles. Don’t be your own.
Don’t fail to suck – Skill comes from showing up, being willing to be bad at something, and learning through the reps.
Fail—a lot – Treat every attempt as a step forward. Progress lives on the edge of what’s uncomfortable.
Fail fast – Shrink the window between attempts. Learn quickly. Adjust. Keep moving.
Fail publicly – Let people see your effort. Normalize the process. Inspire others with your courage.
The battlefield taught me that failure is part of the formula. But so has business. And fatherhood. And faith.
The Steady Leader isn’t about avoiding failure—it’s about staying clear-headed when the pressure hits. It's about leading yourself with intention so you can lead others well.
And sometimes, that means stepping into the dark, not knowing if the intel is real, but going anyway.
Where are you holding back because you're afraid to fail?
What if the risk of failure is actually your gateway to something meaningful?
Stay steady,
Schuyler
Written by Schuyler Williamson
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God Bless!
~ Schuyler Williamson