Leadership Lesson 25 – Celebrate Failure
Fail Fast. Learn Faster. Lead Better.
One of the most surprising parts of leadership is this:
your greatest lessons rarely come from perfection—they come from the moments that didn’t go as planned.
Somewhere along the way, many of us start believing we need to be flawless. We overthink, over-plan, over-edit, and over-analyze… all in the hope of avoiding mistakes. We convince ourselves that if we just refine things a little more, we’ll finally “get it right.”
But here’s the truth:
You will fail.
And trying to out-plan failure only slows down your progress.
When we get stuck in “paralysis by analysis,” we don’t eliminate mistakes—we only delay them. And in the process, we delay growth, innovation, and the momentum that leads to real success.
Encourage Failure Early and Often
Success speeds up the moment we stop fearing failure and start using it.
Failure gives us data.
It gives us clarity.
It gives us direction.
Every attempt that doesn’t work reveals something valuable:
what won’t move us forward—and what might.
When leaders embrace failure instead of avoiding it, something powerful happens:
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Teams become curious instead of cautious
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People take ownership instead of hiding mistakes
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Innovation becomes normal, not accidental
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Momentum replaces hesitation
Failure isn’t the opposite of success.
It’s one of the fastest paths to it.
This Week’s Action Step
The next time someone on your team brings you a mistake, try asking:
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What did you learn?
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What are you going to try next?
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How quickly can you test it?
These three questions shift the focus from blame to growth—and from fear to action.
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