The Pursuit of Failure: Why Great Leaders Don’t Chase Perfection – Neither Do I
As I celebrate my 63rd birthday on 11/14, I’m reminded of a truth that has shaped every meaningful turn in my life, my leadership, and my work: Success does not come from the pursuit of perfection—but from the pursuit of failure.
Not reckless failure. Not careless failure. But intentional, informed, strategic failure—the kind that teaches, redirects, strengthens, and frees. I'm talking about living just beyond the edge of courage.
Pursuing failure means stepping outside my comfort zone, releasing identities that offer a false sense of safety, and risking familiarity for the sake of growth. Pursuing failure is choosing the kind of stretch that strengthens you, even when the outcome is uncertain.
We talk often about “learning from mistakes,” but few leaders are taught how to fail. Many of us are socialized, including in our homes, to seek flawless execution, spotless records, and uninterrupted upward trajectories. Yet, the leaders who rise highest are the ones who know when and how to fail.
Where I Found Failures
I’ve found failure in the tension between who I was expected to be and who I was becoming. It still comes in the silence before I speak my uncomfortable truth, and in the moments I risk being misunderstood rather than staying small.
One of my biggest failures came after my decision to live openly as a survivor of childhood sexual abuse. I spent years estranged from my family. At the time, it felt like failure was the price of freedom. It seemed that honesty had cost me belonging.
But where distance met growth, failure transformed into empowerment. The quiet maturity that healing brings, even in my 60s, taught me that restoration rooted in truth carries more strength than belonging rooted in silence.
When Leaders Pursue Failure
Leaders encounter failure in negotiations, policy decisions, organizational pivots, and those private moments when they must choose between what looks right and what is right. What appears from the outside as a misstep may, from the inside, be the clearest act of discernment.
But in corporate rooms, school districts, political offices, and even family decision-making, we often misunderstand failure as:
• A sign of weakness
• A loss of control
• A lack of competence
• A disqualification from leadership
On the other hand, great leaders, those who are adaptive, strategic, and emotionally empowered, see things differently. Sometimes the highest form of leadership is choosing the “failure” that preserves energy, dignity, trust, or long-term gain.
This is not giving up, it's giving direction. The greatest leaders choose which battles are worth fighting and which losses are worth taking.
We don’t have to treat failure as a verdict. We can explore it as intelligence — data that guides the next iteration of our leadership, our purpose, and our growth.
What If the Democrats Didn’t Fail?
Right now, many are debating whether the Democrats “failed” by voting to end the government shutdown without securing a stronger resolve. The public conversation frames the decision as capitulation. I sure did when I heard it. But what if it wasn’t?
What if it were a strategic pause? What if it prevented deeper harm? What if it created space for a more sustainable path? What if their decision exerts a form of leadership that values people over political performance?
Leadership is stewardship. And stewardship sometimes means choosing an imperfect solution to avoid irreversible damage. Not every loss is a failure. Not every win is wise.
Failure is a Leadership Skill
Great leaders pursue failure because it encapsulates the skills required to lead: emotional maturity, strategic clarity, courage, and self-trust. Leaders who know how to use failure:
• Release what no longer serves their mission
• Avoid unnecessary battles
• Conserve resources for the long game
• Prioritize people over ego
• Adapt when conditions shift
• Signal strength through flexibility
These are the leaders who build resilient organizations. They create cultures where innovation is possible, accountability is upheld, and progress outpaces perfection.
Failure Is Significant, Not Determinant
At 63, I’ve lived long enough to experience both celebrated wins and quiet losses. I’ve written seven books, but only two became best-sellers. I trained for marathons for years; I completed my last one at age 62, but can no longer run pain-free. Am I a failed runner? Of course not.
I also did not pass my third-degree black belt test the first time I took it. But I went on to earn my fourth-degree black belt. Am I a bad martial artist? No!
I dated a man for five years and didn’t marry him; I’ve now been married to my husband for 35 years. Does that mean I didn’t understand love? Absolutely not!
These failures were not endings. They were foundations. Failure is significant, but it is not determinant. It tells you something, but it doesn’t tell you everything.
Each “failure” shaped a different part of my strength. Each taught me what perfection never could. Each was an intentional departure from something that no longer fit, no longer served, or no longer supported my purpose.
Could Failure Be the Key to Success?
If perfection were the key to success, almost none of us would ever make it. But six decades have taught me something far more liberating: It is our relationship with failure—not our avoidance of it—that shapes who we become.
The failures we grow from, the failures we learn from, and the failures we choose strategically are the ones that open the door to our most significant breakthroughs.
Over the years, I’ve learned to surrender battles that were never mine to fight, to release roles that no longer reflected my truth, and to depart from expectations that dimmed my light. Even if the departure felt like a failure at the time, each one clarified my path. And I've come to realize this:
The Power of Departure is the closest any of us will ever get to a guaranteed win.
Because when I learned to let go with intention — when I released expired commitments I was holding onto out of habit or fear — I got out of my own way. I rose clearer and stronger and more aligned with the life I'm meant to lead.
A Leadership Call to Action
As we navigate political turbulence, organizational change, and personal evolution, let’s stop asking: “Who failed?” And start asking: “What did we learn? What did we protect? What did we preserve for the long game?”
Because the leaders who thrive are not chasing perfection, they are pursuing the courage to fail wisely, boldly, and intentionally.
And that—more than anything—is what success is built on.
About the author: I’m Dr. Rosenna Bakari—author of Seven Exits: Leaving Behind What No Longer Serves You, empowerment psychologist, and leadership consultant helping individuals and organizations master the art of departure. My work bridges emotional wellness, leadership, and transformation, guiding people to release outdated patterns so they can lead with clarity and purpose. If you believe that growth requires courage and that failure is part of power, follow me here on LinkedIn for insights on empowerment, leadership, and the psychology of transformation.