The most successful leaders share an unlikely trait: they’ve failed more than most people even try. While conventional wisdom tells us to avoid failure at all costs, the most resilient leaders have learned to do something counterintuitive—they’ve made failure a fundamental part of their lifestyle.
This isn’t about glorifying mistakes or being reckless. It’s about fundamentally reframing what failure means and how we respond to it. When leaders shift from seeing failure as a verdict to seeing it as data, everything changes.
The Resilience Paradox
Here’s the paradox: the leaders who fear failure least are often the ones who’ve failed the most. They haven’t developed thick skin or learned to ignore pain. Instead, they’ve built something more valuable—a different relationship with setbacks entirely.
Sara Blakely, founder of Spanx, credits her father with this mindset. At dinner each night, he would ask his children what they failed at that day. If they had nothing to report, he was disappointed. The message was clear: not trying was the real failure. This early conditioning helped Blakely persist through years of rejection before Spanx became a billion-dollar company.
From Fixed to Fluid Identity
Most people tie their identity to their successes. When they fail, it feels like a fundamental statement about who they are. Resilient leaders do the opposite—they separate their identity from their outcomes.
This distinction is crucial. When your self-worth depends on never failing, you become risk-averse, defensive, and ultimately stagnant. You optimize for looking good rather than getting better. But when you view yourself as someone who experiments, learns, and adapts, failure becomes information rather than indictment.
The Practice of Productive Failure
Embracing failure as a lifestyle means actively practicing it. This looks different than you might think:
Normalize the post-mortem. The best leaders conduct failure autopsies without blame. What happened? What did we expect? What did we learn? These aren’t finger-pointing sessions but genuine explorations of cause and effect. Companies like Pixar hold “notes meetings” where creative work is systematically critiqued, creating a culture where feedback isn’t personal—it’s part of the process.
Set “failure quotas.” Some innovative companies actually require teams to run a certain number of failed experiments. Amazon’s Jeff Bezos has long championed this approach, arguing that if you’re not failing, you’re not innovating enough. When failure becomes expected rather than exceptional, teams become bolder.
Share the stories. Leaders who publicly share their failures—not in a performative way, but authentically—give their teams permission to take risks. When employees see that setbacks didn’t destroy their leader’s career, they feel safer experimenting themselves.
The Metabolic Rate of Learning
Think of failure as the metabolic rate of learning. Just as a higher metabolism processes food faster, leaders who fail more frequently process lessons faster. They’re not smarter or more talented—they’re simply running more experiments and extracting more data from their environment.
This accelerated learning creates compound advantages over time. While others are still protecting their first major initiative, leaders who embrace failure are already on iteration seven, armed with insights their competitors won’t discover for years.
The Emotional Infrastructure
None of this works without emotional infrastructure. Embracing failure as a lifestyle doesn’t mean becoming numb to disappointment. It means building practices that help you process setbacks constructively.
Many resilient leaders maintain some version of these practices: they have trusted advisors who provide perspective, they journal to externalize difficult emotions, they maintain physical routines that stabilize mood, and they actively manage their self-talk. When failure happens—and it will—they have systems to keep moving forward rather than spiraling.
When Failure Isn’t the Teacher
It’s worth noting that not all failures teach valuable lessons. Sometimes you just get unlucky. Sometimes external factors overwhelm good strategy. Resilient leaders understand this distinction. They extract lessons where they exist and accept randomness where it doesn’t, rather than torturing themselves searching for meaning in meaningless setbacks.
Building Organizations That Fail Well
Individual resilience matters, but organizational culture matters more. Leaders who truly embrace failure as a lifestyle work to build systems that support intelligent risk-taking throughout their organizations.
This means creating psychological safety so people can admit mistakes early, before they become crises. It means rewarding learning rather than just results. It means designing processes that allow for small failures that prevent catastrophic ones—the engineering principle of “failing fast” applied to organizational life.
The Long Game
Perhaps the deepest insight about failure and resilience is this: embracing setbacks isn’t really about failure at all. It’s about playing a longer game than everyone else.
When you’re optimizing for never failing, you’re playing a short-term game. You choose safe projects, conventional strategies, and proven approaches. You might succeed steadily for a while, but you cap your growth.
When you embrace failure as part of your lifestyle, you’re playing an infinite game. You’re optimizing for learning, adaptation, and eventual breakthrough rather than consistent approval. Some years look like setbacks. But over decades, this approach compounds into wisdom, resilience, and ultimately, transformational leadership.
The Invitation
The invitation isn’t to seek out failure for its own sake or to be careless with resources and people’s trust. It’s to stop letting the fear of failure make your decisions. It’s to build a life and career where setbacks are expected, examined, and integrated rather than hidden, denied, or catastrophized.
The most resilient leaders aren’t those who’ve never failed. They’re the ones who’ve failed so often, and learned so much in the process, that setbacks have become just another day at the office—uncomfortable, sometimes painful, but ultimately just part of the work.
In a world that’s changing faster than ever, this might be the only sustainable approach to leadership. The question isn’t whether you’ll fail. It’s whether you’ll let those failures teach you, or whether you’ll spend your energy pretending they never happened.