There comes a point where you get tired of the noise, the performance, and leadership being reduced to slogans, gimmicks, and quick fixes.
Over the past couple of years, I have been on a journey of searching, grappling, and wrestling with what it truly means to lead while remaining human-centered. I have written about it, spoken about it, and lived it through moments of clarity and moments of failure. Through it all, one truth continues to rise to the surface. Leadership is deeply human work, and too often that humanity gets lost.
This new project is a response to that realization.
I am deeply grateful to be on this journey with Dr. Donya Ball. What we have built together did not come from a strategy session or a content plan. It came from connection. It is the kind of connection that you recognize immediately and trust without hesitation.
Have you ever experienced that moment in music when you are in the middle of a jam session and someone takes the song in a direction that resonates with you? You lock eyes, exchange a nod, and realize that you are hearing the same thing. In that moment, a shared language emerges and you continue playing, knowing something meaningful is unfolding.
That is what this collaboration has felt like.
Donya and I found that same kinship, and out of that connection, “Real Riffs” was born.
This is not just another leadership podcast.
“Real Riffs” is built for you.
We are creating a space for real conversations about leadership without stunts, product placements, or games. We are committed to honest dialogue about the work, the weight, the joy, and the failures that come with leading. There are conversations that are not being had, topics that are being avoided, and truths that are being softened to fit a narrative. Leaders deserve better, and you deserve better.
“Real Riffs” is an open invitation.
We want to hear from you. We invite you to share the questions that stay with you, the challenges that keep you up at night, and the moments that push you to reflect and grow. You can share your ideas in the comments here, email me directly at sgaillard84@gmail.com, or reach out through direct message on social media to me or to Donya. You can also connect with Donya and learn more about her work at https://www.donyaball.com/.
We are not talking at you. We are building “Real Riffs” with you.
This podcast is designed to reach beyond education because leadership is not confined to a single profession. This space is for anyone doing the work of leading and striving to stay grounded in what matters most.
“Real Riffs” will launch in April, with new episodes released monthly.
Each episode will be approached like an album. We will drop the needle and let it play. Your questions will guide the direction, and your voice will help shape the sound. What emerges will be something real, something shared, and something worth holding onto.
This is your invitation to join the jam.
Bring your questions. Bring your experiences. Bring your truth.
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.
Some days do not arrive with the triumphant swell of “Gonna Fly Now” from Rocky. Some days move with less momentum and more contemplation.
Over the last several months, I have been seeking connection, meaning, and understanding as I wrestle with the mixed emotions of grief and empowerment. Walking away from a role that was breaking my heart and impacting my health required courage. There are days when I feel the strength of that decision. There are other days when I am reminded of failures, shortcomings, and mistakes.
Miles Davis once said, “Do not fear mistakes. There are none.” During a concert in the 1960s with his Second Great Quintet, that philosophy became visible in real time. Herbie Hancock struck what he believed to be a wrong note on the piano. He braced for Miles to glare at him or turn away. Instead, Miles responded by playing notes on his trumpet that reframed the so called mistake. He did not correct Hancock. He absorbed the moment and transformed it. In doing so, he gave Hancock belonging and permission to continue.
I have written before about this moment. I have also reflected on similar moves by Duane Allman and other musicians who leaned into mistakes rather than shrinking from them. These moments have long stood for me as emblems of human centered leadership. They demonstrate that belonging is created not by perfection, but by response. The best leaders know how to meet imperfection with presence.
I remember a similar moment during my first gig with The Skydogs. In the middle of an energetic rhythm section, my hand slammed awkwardly against my guitar. The band paused for a split second. What could have been embarrassment became improvisation. I began striking the body of the guitar like a conga drum. The band joined in, and what began as a mistake turned into a wild percussion breakdown that I still smile about more than thirty years later.
Leadership requires that same posture.
We operate in spaces driven by metrics, evaluations, and constant measurement. Perfection becomes a quiet trap that drains the marrow from leaders who care deeply. When mistakes happen, the instinct is often to retreat, self criticize, or withdraw.
Leadership is lonely on certain days. When failure visits, that loneliness can intensify in ways that feel overwhelming.
Yet failure is not proof that we are unqualified. It is proof that we are engaged. Mistakes are not verdicts. They are invitations to respond differently.
What might happen if we made that move the norm rather than the exception? What would it look like to build cultures where leaders instinctively play the wrong note back with grace? How might our schools, teams, and organizations change if belonging was reinforced in moments of error rather than withheld?
We need more leaders who know how to transform a misstep into momentum. We need more pauses in the mania. We need more small moments of belonging that remind us that growth does not require perfection.
Leading while human means accepting that we will strike the wrong key from time to time. What matters is how we respond, and how we respond to one another.
Some connections are for a season. They help us grow, reflect, and find our footing. Then, sometimes, the paths quietly diverge.
I am learning that clarity around values can be both grounding and lonely. It does not mean anger. It does not mean judgment. It simply means paying attention to what no longer fits.
I am choosing to keep moving toward what aligns with who I am becoming. I am choosing alignment over approval. I am choosing peace over proximity. With gratitude for what was. With honesty about what is.
This is a weekly space where I connect music, grooves, and stories. Albums that sit with us. Songs that carry us. Records that feel like companions in certain seasons of life.
I am not waiting anymore. I am building the space I wish existed.
Season One begins this week.
If you love music that means something, then you belong here.
There is a place I often call Principal School. It is the imaginary training ground where we believe all the lessons of leadership will be handed to us before we ever step into the role. Over time, I have learned that some of the most important lessons are never taught there at all. They are learned the hard way, often quietly, and sometimes at great cost.
One of the biggest myths perpetuated in school leadership is that there is a single way to lead well. I bought into that myth for far too long. I watched other principals on social media and began to believe that if my style did not look like theirs, then I must not be good enough. I measured myself against highlight reels instead of my own values. That comparison and pressure sent me to the emergency room twice. It took a toll on my body, my mind, and my spirit.
Another lesson they do not teach you in Principal School is that leadership can slowly pull you away from the very relationships that sustain you. I regret not investing the time I once did in friendships. I regret choosing email replies and late night work over phone calls and shared meals. I felt the weight of that loss deeply over the last few years when the invitations stopped coming. I am grateful for the meaningful friendships I still have, even though many of them live far away. Today, I cherish every text message, every phone call, and every Zoom conversation because I know how easily those connections can fade when duty becomes all consuming.
I also regret the moments I missed with my wife and daughters. There were times when I chose the principalship over being fully present with them. That truth is hard to name, but it matters. You blink, and your children are grown and moving out of the house. You do not get that time back. Now, I cherish my family even more, and I hold our time together with greater care and intention than ever before.
For my physical and mental health, I made the decision to step away from the principalship. I returned to my assistant principal roots and found something I had lost along the way. I found myself again. I am happier, healthier, and more grounded. I have grown in my therapy work and remain deeply committed to it. That commitment has helped me reconnect with my core, my purpose, and my humanity. The version of leadership I was living was not aligned with who I am or how I want to live. In trying to be everything for everyone at school, I lost sight of who I needed to be for myself and for the people who love me.
Recently, in a conversation with Dr. Andrea Trudeau, a phrase stayed with me. We need to rescript the narrative. Human Centered Leadership is not widely accepted in some spaces, and I am fully aware of that. Still, I am determined to disrupt the conversation in a good way. Leadership does not have to cost you your health. It does not have to require the sacrifice of your family or your friendships. Human Centered Leadership is not only about how you serve others. It is also about how you care for yourself and how you show up for those who cherish you as a spouse, a parent, and a friend.
I learned these lessons the hard way. I do not want others to have to do the same. My purpose now is simple and deeply personal. If these words help one leader put their phone down and spend time with their child, then I have done my job. If they help one leader step away from email long enough to call a friend, then I have done my job. If they help one person avoid being rushed to the hospital from the schoolhouse like I was, then I have done my job.
This post will not go viral. It will not collect metrics or applause. That is not the point. Leadership does not have to be lonely. Leadership does not have to break you. You can lead with love. You can protect your humanity. You can serve others well without losing yourself along the way.
This reflection is not the end of the conversation for me. It is the beginning of a deeper commitment to naming what matters and creating space for a more human way to lead. One of the ways I am continuing this work is through a new podcast series I am co- hosting with Dr. Sonia Matthew called Leading While Human.
Our first episode drops on February 1 and features a powerful conversation with Dr. Rachel Edoho-Eket. Throughout February, we will release a new episode every Sunday with guests including Lauren Kaufman, Dr. Donya Ball, and Principal Kafele. Each voice brings wisdom, honesty, and lived experience to the question of what it truly means to lead while human.
Leading While Human will be a quarterly podcast. Each series will feature four guests and four conversations designed to slow us down, ground us, and remind us that leadership does not have to cost us our health, our relationships, or our humanity.
I am grateful for the opportunity to learn alongside these voices and to invite others into this space. Stay tuned for what comes next as we continue to rescript the narrative on leadership together, one human centered conversation at a time.
Lately, I have been thinking deeply about leadership and where the conversation has drifted. Somewhere along the way, leadership became confused with performance. It became about big voices, bigger platforms, viral moments, staged selfies, best selling books, and canned keynotes. It became about stunts and acrobatics designed for attention rather than impact.
That version of leadership is not sustainable, and it is not humane.
Leadership is not a social media highlight reel. Leadership is not defined by beleaguered metrics, fluctuating test scores, or anonymous survey data stripped of context and humanity. Leadership is not about being the loudest voice in the room or the most visible person on the stage. Chasing those myths of leadership can cost you your nervous system, distance you from the people you love, and leave you with an empty shell of what leadership was meant to be.
I know this because I lived it. That path sent me to the hospital twice.
There was a time when toxicity, doubt, and Impostor Syndrome defined far too much of my leadership experience. I bought into a broken paradigm that told me I had to prove myself constantly and that rest was a weakness. I believed that my value as a leader was tied to outcomes I could never fully control. That way of leading led to exhaustion, anxiety, and a version of leadership that felt hollow and unsustainable.
Thankfully, I have moved away from those times and places.
Through prayer, therapy, fitness, and intentional work on my own humanity, I am learning to lead differently. I am learning to slow down and to listen more deeply. I am learning to honor liminal spaces instead of rushing through them. I am learning to be present in the moment rather than constantly chasing what comes next. Most importantly, I am learning to value my own humanity so that I can better recognize and support the humanity in others.
This is the leadership conversation that I believe must be disrupted and reimagined.
Leadership, at its core, is relational. Leadership is guided by empathy, kindness, and a deep sense of belonging. Leadership is not about perfection or performance. Leadership is about presence. Leadership is not about having all the answers. Leadership is about creating spaces where people feel safe enough to ask honest questions and be fully seen.
From these reflections and lived experiences, something meaningful has emerged.
I am deeply grateful to be co-hosting a new podcast series with the amazing Dr. Sonia Matthew called Leading While Human. This special series debuts on February 1 and comes straight from the heart. Together, we are creating space for honest conversations about what it truly means to lead while human.
Our inaugural series features four voices I deeply admire: Dr. Rachel Edoho-Eket, Lauren Kaufman, Dr. Donya Ball, and Principal Kafele. We will release a new episode every Sunday throughout February, and we will return four months later with four additional guests to continue the conversation.
This work matters deeply to me because it is personal. It is born from struggle, healing, and a firm belief that leadership must return to its human roots if we are going to build schools, organizations, and communities where people can truly thrive.
If you would like to hear my reflections on Leading While Human, you can listen to or watch the latest episode of Leadership Liner Notes on the platform of your choice.
My hope is that this reflection invites you to pause, reflect, and reclaim a version of leadership that honors who you are as a human being first. We do not need more performances. We need more presence. We do not need louder voices. We need deeper listening. We do not need leadership myths. We need leadership rooted in meaning, care, and humanity.
Some mornings arrive heavier than others. You wake up carrying more than you expected, unsure where the weight came from, only knowing that it is there. In those moments, the quiet around your work, your words, and your efforts can feel louder than any criticism. This reflection comes from one of those mornings.
This blog post is a form of self-talk for me. It is equally written for anyone else who is struggling quietly right now.
Leadership can be deeply meaningful, but it can also be profoundly lonely. We are encouraged to share our thinking, our learning, and our growth. We are reminded that vulnerability builds trust and that authenticity matters. Still, there are times when we share something heartfelt. We direct it toward others or put it into the world with care, and nothing comes back. That absence can hurt in ways that are hard to explain.
I have learned that sometimes our ideas are not heard in our own backyard. That realization can sting, especially when the words came from a sincere and hopeful place. It is also why it is essential to find spaces and platforms where your voice can breathe. For me, that space is writing. It is blogging. It is podcasting. These are the places where I process, reflect, and continue learning out loud.
It is easy to fall into the trap of measuring impact by numbers. Views. Downloads. Likes. Shares. Over time, those metrics can quietly convince us that our work only matters if it reaches a certain volume. I am still unlearning that thinking. Today, I remind myself of something simple and grounding. If one person finds what they need in something I share, then the work has meaning. If one person feels seen or steadied for a moment, then the effort was worth it.
This reflection is a reminder to keep showing up anyway. It is an invitation to keep sharing your thoughts even when the response is uneven or delayed. It is a quiet act of trust in the belief that someone is listening, even when you cannot see them. The work of leadership is not about being the loudest voice in the room. It is about being a steady one.
I am writing this to remind myself that my voice still matters on the days when it feels unseen. I am also writing it for anyone else who needs permission to keep going without guarantees. The quiet does not mean you failed. Sometimes it simply means your words are traveling, settling, and finding their way to the right person at the right moment.
Hope does not always arrive with applause. Sometimes it shows up as resolve. Sometimes it shows up as consistency. Sometimes it shows up as choosing to center people over metrics and meaning over momentum.
For today, choosing to stay human in the work is enough.
There are albums that arrive in your life right on time. There are also albums that feel as if they have been waiting for you all along.
Neil Diamond’s Gold is that kind of record for me.
It was recorded live at the Troubadour on Santa Monica Boulevard in July of 1970. Just about ten miles away, in Inglewood, I was two months old and brand new to the world. I did not know it then, but something meaningful was happening nearby. A voice was finding its footing. A performer was stepping into himself. A bridge was being built toward what would come next.
I did not discover Gold until my junior year of college. I found it in a used record store in Washington, D.C., sometime around 1990 or 1991. I remember taking it back to my dorm room. I lowered the needle and felt something familiar. It was something I could not yet name. Even then, it sounded like an album caught between chapters. Confident, yet searching. Grounded, yet reaching.
That feeling has only deepened with time.
Gold captures Neil Diamond in a liminal season. He was between record labels. He had experienced success in the 1960s, yet the full arc of his 1970s creative breakthrough had not fully arrived. This was not a greatest hits collection, even though the title suggests one. It was something far more human. It was a document of becoming.
The band matters here. Carol Hunter’s guitar work has a raw edge. It gives the music a sense of forward motion. Her style was shaped by time alongside artists like Bob Dylan. Eddie Rubin’s drumming, informed by deep jazz roots and work with artists like Billie Holiday, brings both restraint and release. Randy Sterling’s bass provides an anchor that allows everything else to breathe. This was a group capable of listening, responding, and taking risks in real time. That truth is audible.
Then there is “Lordy.”
That song feels like a door being pushed open. Gospel-inflected. Theatrical. Unfiltered. It hints at the ambition that would soon fully emerge on Tap Root Manuscript. On this album, “Cracklin’ Rosie” would become Neil Diamond’s first number-one hit. “The African Trilogy” placed on Side 2 of that album would expand his songwriting into something expansive and cinematic. “Lordy” is not the destination. “Lordy” is the signal.
This is why Gold resonates so deeply with me right now.
I find myself in my own in-between season. Years of experience remain present. Familiar structures are loosening their grip. Listening has become more important than certainty. This album reminds me that the middle matters. The bridge is not wasted time. Confidence is often built quietly in rooms that do not yet resemble arenas.
My connection to Gold also brings to mind the film Song Sung Blue. I love that movie deeply. The film is based on the real life story of Mike and Claire Sardina, who form a Neil Diamond tribute band known as Lightning & Thunder. Watching the two main characters played by Hugh Jackman and Kate Hudson is profoundly life-affirming. They challenge the impossible until it becomes possible. The film honors persistence, hope, and belief without irony. It treats becoming with dignity. The music performances are truly “so good, so good!”
That same spirit lives inside Gold.
This record honors the becoming.
This post accompanies the latest episode of #LeadershipLinerNotes. In it, I share more about this album and the Troubadour. I explain why this particular season of my life feels so closely tied to it. You can listen to the podcast version here: Spotify/Megaphone:
I would love to know what your Gold has been. Was there an album, moment, or season that met you in the middle? Did it quietly remind you that something meaningful was still unfolding? Please share in the comments. I would love to hear from you.
Sometimes the gold is not found at the beginning. Sometimes the gold is not waiting at the end. Sometimes the gold lives right in the in-between.
Some blog posts arrive quietly. Others land with weight and warmth.
When Lauren Kaufman’s latest post, People Come First, landed in my inbox, I paused before opening it. Not out of hesitation, but out of trust. I knew, just as I always do, that I would walk away feeling enriched. I would feel inspired. I would be nudged to be better in my own practice after reading her words.
That has been the gift of being a long time reader of Lauren’s work. It has also been the gift of friendship and thought partnership with Lauren.
Lauren Kaufman is a district leader, a disciplined weekly blogger, and the author of the inspiring book The Leader Inside. She is also someone who writes from lived experience, not from a pedestal. Her posts are never about performance. They are about presence.
Her blog consistently shows up with clarity and heart. When her writing lands in my inbox, I know I will be enriched, inspired, and motivated. Lauren has a way of making her words resonate so deeply that you want to do better and be better.
In People Come First, she reflects on a poignant exchange with another human being. The moment is simple on the surface, yet profound in its implications. The post does not rush toward resolution. It does not offer a checklist or a framework. It invites the reader to slow down and sit with what it truly means to show up for someone else.
That restraint is precisely what makes it powerful.
Here’s the Core of What It Shows
At its heart, this post is about listening. Not listening as a leadership move or a strategic tool, but listening as an act of humanity.
As I continue to delve deeper into human-centered leadership, Lauren’s words echoed something I have been reflecting on myself. Sincere and deep listening is not an accessory to leadership. It is an entry point.
To listen well is to communicate worth. To listen deeply is to make space. To listen without fixing is to honor someone’s story.
Lauren reminds us that people do not need us to be impressive. They need us to be present.
What This Stirred in Me
Reading this post led me to reflect on how often leadership culture rewards speed over stillness. We are praised for having answers, for moving quickly, and for resolving things efficiently.
The leaders who have shaped me most were the ones who slowed the moment down. They listened without interruption. They stayed curious. They did not rush me toward clarity before I was ready. Lauren is one of those leaders for me and so many others.
Lauren’s post reinforced a truth I am still learning. Human centered leadership begins long before we speak. It begins in how we listen.
A Thought Partnership That Matters
Lauren is also my most frequent guest on my podcast, Leadership Liner Notes, and the unofficial executive producer of the show. Our conversations consistently ground me and stretch my thinking.
One of our most recent episodes was a co-hosted conversation celebrating and amplifying the work of Elizabeth Dampf, author of Am I Cut Out for This?. The episode explored self doubt, courage, and staying rooted in purpose.