Failure or Success? Redefining What Winning Really Means in Leadership

Failure or success—it’s a question that sparks strong opinions and even stronger emotions. This topic recently comes up during leadership meetings on a pretty regular basis, and it’s one worth exploring far beyond the conference or training rooms. As leaders, how you define success—and failure—shapes your mindset, your decisions, and ultimately your outcomes.
From an early age, you were taught that success means near perfection. In school, an “A” represents success—usually getting 9 out of 10 answers correct. An “F,” on the other hand, signals failure—less than 6 correct. Everything else falls somewhere in between, creating a clear, structured grading system that tells you where you stand.
But once you step outside the academic environment, those definitions start to blur.
When Failure Is Actually Success
Consider the game of baseball. Even the best hitters in the world fail more often than they succeed. A strikeout, a fly ball, or being thrown out at first base all count the same: an out. In fact, if baseball used academic grading standards, most Hall of Fame players would be considered failures.
The last Major League Baseball player to hit over .400 in a season was Ted Williams in 1941. Over a remarkable 19‑year career, Williams finished with a lifetime batting average of .344 and is widely regarded as one of the greatest hitters of all time. That means he failed to get a hit in more than 65% of his official at‑bats.
Think about that for a moment!
Someone who “failed” nearly two‑thirds of the time is celebrated as one of the best ever. Why? Because success is defined by the arena in which you compete.
Leadership Isn’t About a Perfect Record
In leadership, it’s easy to become overly focused on wanting to “hit the ball” every single time. You want every decision to be right, every initiative to succeed, and every outcome to be positive. When that doesn’t happen, you label the experience as failure—and often take it personally.
But leadership doesn’t work that way.
Progress requires action, and action always carries risk. The true measure of success isn’t perfection—it’s growth, learning, and resilience.
Few examples illustrate this better than Thomas Edison. Often considered one of the greatest inventors of all time, Edison reportedly failed over 10,000 times before successfully inventing the light bulb. When questioned about those failures, Edison famously reframed the narrative, explaining that he didn’t fail 10,000 times—he simply discovered 10,000 ways that didn’t work.
Imagine how different the world would be if Edison had stopped after the first hundred attempts. Or the first thousand.
Reframing Failure as a Leadership Tool
For leaders, failure should never be an endpoint—it should be a teacher. Many of life’s greatest successes are built on lessons learned during moments you initially label as setbacks.
The key is perspective.
When you define success and failure within the context of the “big picture,” you gain clarity. Temporary setbacks don’t disqualify you; they refine you. Missteps don’t end the journey; they redirect it.
The only true failure is choosing not to act at all.
As a leader, you must be willing to step up to the plate and swing—knowing full well you won’t connect every time. Growth doesn’t come from standing still. It comes from engagement, effort, and the willingness to learn.
Final Thoughts for Leaders
Denis Waitley captured this truth perfectly:
“Failure should be our teacher, not our undertaker. Failure is a delay, not defeat. It is a temporary detour, not a dead end. Failure is something we can avoid only by saying nothing, doing nothing, and being nothing.”
And legendary coach John Wooden added a powerful reminder:
“Failure isn’t fatal, but failure to change might be.”
Leadership success isn’t about avoiding failure—it’s about responding to it. Learn from it. Adapt. And keep swinging.
Leadership Void exists to challenge how we think about leadership—especially in the moments that don’t come with clear answers.
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Leadership isn’t about titles or perfect circumstances. It’s about what you do next.
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