Failure and The Work That Remains

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.

I will keep going.

Failure and Identity

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.

What I know is this.

Walking away did not end my story.

It helped me find it.

“Real Riffs”: Finding the Signal in the Noise

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.

Let’s create something that matters.

The Leadership I Lived and The Human-Centered Leadership I Choose Now

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.

Finding Your Voice in the Silence: A Leader’s Reflection

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.

Still Learning: Coffee and Creating Third Spaces

“Starbucks CEO Announces A Huge Change to Win Back Customers”- https://www.inc.com/leila-sheridan/starbucks-ceo-announces-a-huge-change-to-win-back-customers/91284147

Why This Article Is Worth Your Time

This “Inc. Magazine” piece goes beyond business strategy and gets at something deeper: the human need for connection. The idea of the third place reminds us that people are not looking for more transactions. They are looking for places and cultures where they feel seen, welcomed, and able to belong.

That idea matters far beyond coffee shops. I do appreciate the intentionality Starbucks is doing to create a meaningful and human-centered experience for their customers.


Here’s the Core of What It Shows

When organizations intentionally design spaces that invite people to slow down, connect, and stay awhile, trust and loyalty follow. The article reinforces that strong leadership is not about efficiency alone. It is about creating environments where relationships can take root and people feel grounded.

That is the heart of human centered leadership.


Why This Connects to My Work

This concept echoes the work I collaborated on with Dr. Andrea Trudeau during our ISTE+ASCD Webinar Series and poster session at the ISTE+ASCD Conference in San Antonio. It also aligns closely with the conversations Dr. Sonia Matthew and I are exploring in an upcoming podcast series focused on human centered leadership.

Whether in schools, organizations, or communities, leaders shape the culture by shaping the spaces people experience every day.


Bottom Line

Leadership is not just what we measure or manage. It is what we build for people to gather, connect, and belong. This article is a timely reminder that presence still matters and so does place.

🔗 https://www.inc.com/leila-sheridan/starbucks-ceo-announces-a-huge-change-to-win-back-customers/91284147

Let me know your thoughts and learning on this article. You are invited to the conversation as we are all #StillLearning.