Issue 56: Why Failure Doesn't Mean you've Lost

ISSUE 56

10 SEPTEMBER 2025 | READ ONLINE

Hi Reader,

We’ve all been told: failure is good for you.

Fail fast. Fail forward. Failure is feedback.

And yet, if we’re honest, it rarely feels that way. Most of us still associate failure with losing. Miss the mark? Lost. Get turned down? Lost. Didn’t land the job? Lost.

That’s the paradox: we know failure is part of growth, but it still feels like the scoreboard reads zero.

Reframing the Paradox

Failing is not losing. They are entirely different outcomes.

Failing is proof you were willing to try.
Losing is walking away with nothing.

Failure, at its core, is tuition, and it’s what you pay to gain wisdom. Losing is quitting class before the lesson arrives.

In Chapter 7 of my book, Clarity in Chaos: Lead with Purpose in Disruptive Times, I share this: sparking ideas and letting them fly isn’t about making every idea succeed. It’s about experimenting, learning, and adapting. The failures? They’re the data that makes the breakthrough possible.

The Hidden Pattern Behind Success

James Dyson: He once said, “I made 5,127 prototypes of my vacuum before I got it right. There were 5,126 failures. But I learned from each one.” That wasn’t losing, actually, it was building toward a billion-dollar idea.
Sara Blakely: The Spanx founder recalled, “My dad used to ask my brother and me at the dinner table what we had failed at that week. If we didn’t have something, he would actually be disappointed.” That ritual reframed failure into courage, not defeat.
And me? When I left a senior executive role to join a tech team where I was a beginner, I “failed” often. But I left with skills, resilience, and a whole new trajectory. That’s not losing. That’s leveling up.

This Week, Try This

Name it differently. When something doesn’t go as planned, don’t label it a loss. Call it an experiment.
Ask the better question. Not “Did this succeed or fail?” but “What did I learn?”
Count attempts. Keep track of how many experiments you ran this week, not just the wins. Attempts are the real leading indicator of growth.

Because the leaders we admire most? They didn’t get there by avoiding failure. They got there by refusing to confuse failing with losing.

See you next week,

Megan

P.S. Next time you fail, ask yourself: What did I just gain with this lesson? That’s how you unlock the paradox.