I have been sitting with failure in this season, and it has taken me on a deeper journey than I expected. I am spending time reflecting on my failures in ways that are honest and necessary. I am learning that failure hurts. I am also learning, through John C. Maxwell’s Failing Forward: Turning Mistakes into Stepping Stones for Success, that failure is an event, even when the pain feels personal and lasting. The hurt shows up in real ways. It shows up when I share something meaningful and no one seems to notice. It shows up when I am passed over for opportunities I believed I was ready for. It shows up when I write a blog post and there is clearly no resonance from even friends or loved ones. Those moments can feel like confirmation of failure, and they sting more than I want to admit.
I have been thinking about the idea that a prophet is not always accepted in their own town, and it has stayed with me. I have tried to find traction in familiar places and have come up short more times than I want to admit. I have felt unseen in places where I once felt grounded. I have carried an idealized vision of a band, a space where strengths are valued and belonging is real. I am coming to terms with the reality that this kind of space may not exist for me in my own neighborhood. That realization has been difficult, but it has also been clarifying.
What remains is the work and the responsibility to create what I cannot find.
I will keep writing, keep blogging, and keep podcasting because that is what I can contribute. I am building spaces like “Leading While Human,” the upcoming “Real Riffs,” and The Disruption Table because I am searching for kinship and connection. I am looking to build something that reflects the kind of belonging I know is possible. I may not be tapped for certain opportunities, but I am beginning to see that those missed opportunities may be leading me toward something better, something more aligned with who I am and what I value.
Some days it is easy to hold onto that truth. Other days it is painful.
I believe this work is leading me toward a path where I can help other leaders navigate failure with honesty and courage. I have already begun that work through my writing and my podcasts, and I see it growing into something more. I want to help others lead while human, to make space for reflection, belonging, and truth in a profession that often asks us to hide those very things.
I am learning to ignore the noise and stay focused on what is mine to offer with honesty and care. I know this work is leading somewhere, even if I cannot fully see it yet. My writing is more than expression. It is my way of reaching beyond my immediate surroundings to connect with others who are also navigating failure and searching for belonging.
Failure is part of the story, but it is not the end of it.
This is for the leader who feels like they have lost their place.
In 2007, Robert Plant, lead singer of the most iconic bands in music history, stood on stage with Led Zeppelin at the O2 Arena for what would become one of the most celebrated reunions in rock history. The world wanted more. Promoters offered a massive tour and an even larger payday. The expectation was clear. Step back into the machine. Relive the past. Give the audience what it wants.
Plant walked away.
He chose a different path. He followed his own creative instincts. He leaned into new sounds, new collaborations, and new risks, including his work with Alison Krauss. He stepped away from what the world defined as success and into something that aligned with who he was becoming.
Some called it a missed opportunity. Others called it a mistake.
It was neither.
It was identity.
That moment has stayed with me because it reframes how we think about failure. We are conditioned to believe that turning away from something big, something visible, something validated by others must mean we failed. We attach our worth to outcomes, roles, titles, and applause. When those things shift or disappear, we question who we are.
John C. Maxwell offers a powerful reframe in his work Failing Forward: Turning Mistakes into Stepping Stones for Success. Failure is an event, not a person. That idea has been sitting with me in this season. I have replayed decisions. I have questioned outcomes. I have wrestled with the weight of what did not work. I have felt the tension between what was and what is.
I am learning that failure does not get to define me unless I allow it to do so.
Walking away has been part of that learning.
Walking away from environments that drain rather than develop. Walking away from expectations that do not align with who I am. Walking away from traditional leadership paths that no longer reflect the kind of leader I want to be.
There have been moments when that felt like failure. There have been moments when it felt like I was stepping off a stage with no clear next act.
Those moments have become the catalyst for something else.
Space.
Space to think. Space to reflect. Space to reconnect with why I started this work in the first place. Space to explore new collaborations, new ideas, and new ways of showing up. That space has led to new conversations, new creative work, and new projects, including the podcast I am building with Donya Ball. That work is rooted in something real. It is not built on noise or performance. It is built on truth, reflection, and connection.
That would not have happened if I had stayed where I was.
We have to normalize this.
We have to normalize that walking away from what is toxic is not quitting. It is not weakness. It is not failure. It is an act of clarity. It is an act of courage. It is a commitment to protecting your humanity in spaces that often ask you to leave it behind.
Leadership has too often been framed as endurance at all costs. Stay longer. Push harder. Ignore the signals. Keep performing. That narrative is not only outdated, it is harmful.
There is a different way.
A way that allows leaders to reflect, to reset, and to realign. A way that recognizes that identity is not tied to a title or a role. A way that gives permission to step away in order to step into something more aligned and more sustainable.
I am still in that work.
I am still unpacking what failure means in my own story. I am still learning how to separate what happened from who I am. I am still finding my voice in spaces that value honesty over hype.
Lately I have been reflecting on past failures as a leader. In many leadership circles across social media, conferences, and professional spaces, failure is often mentioned briefly and then quickly reframed as a lesson learned. The story usually resolves neatly, much like a sitcom where the main character faces a conflict and everything wraps up by the end of the episode.
Leadership does not work that way.
Failure in leadership rarely resolves quickly. Even when we fill our days scrolling through inspirational memes about perseverance and growth, the pain still lingers. The hurt continues. Failure does not disappear simply because we choose to frame it positively.
Too often we rush to the happy ending.
Several years ago, the “Famous Failures” memes were widely shared online. I remember drawing inspiration from those images that highlighted the early setbacks of people like Michael Jordan, Oprah Winfrey, and Albert Einstein. One of the examples that resonated deeply with me was the story of The Beatles being rejected by Decca Records before becoming the most influential band in history. A Decca executive reportedly told them that guitar groups were on the way out.
I wrote about that moment in my book The Pepper Effect. I shared that story many times with faculty during my years as a principal because it offered a powerful reminder that rejection and failure often precede greatness. In recent years I have noticed that the story no longer carries the same inspirational weight for some audiences. I sometimes walk away from sharing that anecdote feeling a quiet sense of disappointment. I love The Beatles. I wrote a book about them. I have spoken about their story at conferences and leadership gatherings. At times the response has been enthusiastic. At other times it has been a collection of polite nods.
That realization stings a little. It reminds me that even the stories we believe will inspire others do not always land the way we hope.
Leadership author John Maxwell addressed this tension in his book Failure Forward: Turning Mistakes into Stepping Stones for Success. Maxwell writes, “One of the greatest problems people have with failure is that they are too quick to judge isolated situations in their lives and label them as failures.” He reminds readers that mistakes are inevitable and that mistakes only become true failures when we continually respond to them incorrectly.
Amy Edmondson, a leading voice on psychological safety, explores similar ideas in her book Right Kind of Wrong: The Science of Failing Well. Edmondson encourages leaders to rethink how organizations respond to mistakes and to recognize the potential for growth and discovery that can emerge from them.
Both perspectives resonate with me. I appreciate the wisdom behind them.
Yet the more I reflect on my own experiences, the more I arrive at a simple and honest truth.
Failure sucks.
Failure is painful. Failure can be debilitating. Failure drains energy and confidence. Failure often shows up when we step into bold and unfamiliar territory. It waits quietly beside us as we take risks, stumble, and fall short.
There is not enough honest conversation about the emotional toll of failure. Many leadership conversations focus on the research, the strategies, and the case studies. Those perspectives are important. At the same time, they often overlook the personal hurt that accompanies failure.
Leading while human requires that we acknowledge that pain.
I recently attempted to start a book study for colleagues. No one responded. That moment hurt more than I expected. I think about a conference session where only three people showed up. The room felt far too large for such a small audience. I delivered the session anyway, though the experience was both humbling and uncomfortable.
Moments like those stay with you.
Failure has a way of reaching into the deeper parts of our identity and purpose. It can leave us questioning our abilities and wondering whether we truly belong in the spaces where we serve.
I wish there were a simple antidote.
There are many inspiring stories about overcoming failure. I am curious about John Maxwell’s upcoming book How to Get a Return on Failure: Fail Smarter, Return Stronger. The title alone reflects an important mindset shift. Organizations must build cultures that offer grace, coaching, and support when people struggle or fall short. Many organizations do this well. Others do not. In some seasons of my career, authentic and humane support was inconsistent or absent.
Those seasons can feel incredibly lonely.
During this current liminal season of my life and leadership, I often revisit my own failures. Some moments invite reflection. Some invite reconsideration. Some even invite regret. Those reflections lead me to a deeper question.
How do we remain human centered leaders while staying true to our own humanity?
Perhaps the pain of failure is part of what makes us human. Perhaps the sting becomes the catalyst that pushes us toward growth and perseverance. Charlie Brown runs toward the football again and again, even though Lucy might pull it away at the last moment. He still runs forward with hope.
Leadership sometimes feels exactly like that moment.
Failure invites us to pivot. Failure invites us to step back and reflect. Failure invites us to rediscover the gifts that still live within us. Failure teaches us lessons we could not learn any other way.
Those lessons matter.
At the same time, honesty requires that we acknowledge a simple truth.
Failure still sucks.
Leaders cannot pretend that the pain does not exist. We must acknowledge the hurt. We must allow ourselves moments of reflection and even moments of sadness. We gather ourselves again, roll up our sleeves, and keep moving forward.
Our response to failure ultimately defines us far more than the failure itself.
That is the work.
That is the calling.
That is the gig.
Our response to failure ultimately defines us far more than the failure itself. Leading while human means we acknowledge the pain, gather ourselves, and keep showing up anyway.
Leadership Liner Notes: Sean Gaillard 