Miles Davis

Between What Was and What Is Next

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This is a reflection for anyone who has ever stood in the in-between. The space where purpose meets uncertainty and the next chapter feels just out of reach. These are the moments that call for a leadership reset to pause, reflect, and begin again with renewed intention.

There is a strange stillness in the in-between. It is that quiet moment when one chapter fades but the next has not yet begun.

It is not regret. It is ache. The kind that comes from knowing you are at a crossroads. I have danced with failures and missed opportunities. I have wrestled with the silence that follows when you put your heart into something and it goes unseen. That silence has been my teacher.

I think often of those moments in music when an artist stood in their own in-between. When Miles Davis created Kind of Blue, he was leaving behind the familiar and stepping into something uncharted. He entered what is often called a liminal space, a threshold between what was and what could be. It was risky. It was uncertain. Yet from that space of transition came a timeless masterpiece that changed everything.

Or consider The Beatles during the Let It Be sessions. The band was fractured and weary. Yet in that fragile in-between space they still created moments of truth and beauty. They found the courage to keep recording even when it felt like the music had lost its way. Somehow, that honesty became the song that still echoes across time.

Liminal spaces are where the soul rewrites its melody. They are uncomfortable, but they are also sacred. They strip away titles, roles, and routines until only what is real remains.

What is real right now is that I still care. I still believe in people. I still believe in creativity, connection, and service. I still believe that words matter, even if no one reads them.

This is where the Leadership Reset comes alive. It is something I created and shared in a recent blog post. I was honored to share on a recent episode of the “Teachers on Fire Podcast” with Tim Cavey. It is a simple practice that can help any leader find rhythm again when the noise gets too loud or the silence feels too heavy.

Listen to the full conversation here: Take the 3 Minute Leadership Reset with Sean Gaillard

The 3 Minute Leadership Reset

1. Take a Breath (30 seconds)
Close your eyes.
Inhale slowly and say to yourself:

“I am still here.”

Exhale and say:

“I am enough.”

Do this three times. Feel your shoulders drop. Feel your pulse slow. You have just reclaimed your space in the moment.

2. Anchor in Gratitude (1 minute)
Ask yourself quietly:

What one small moment today reminded me I am alive?
What one connection, a smile, a song, a student, gave me a spark?
What one thing am I proud of, even if no one noticed it?

Write it down in a notebook or say it aloud. That is your leadership echo, a reminder that small actions still ripple outward.

3. Affirm and Reframe (1 minute)
Say these words out loud, slowly and intentionally:

“I am not invisible. I am building something that lasts beyond applause.”
“My work is meaningful, even when it is quiet.”
“The music I make through service, kindness, and creativity still plays, whether or not the crowd is listening.”

Let those words live in your breath. You have just tuned your soul back to the right frequency.

4. Reconnect (30 seconds)
Before moving on with your day, take one small action to reconnect:

Send a short message to a friend or colleague.
Share a kind word with a student or staff member.
Play a song that brings you joy.

These micro moments rebuild our leadership core from the inside out.

Maybe leadership is not about applause or spotlight moments. Maybe it is about keeping the song going when you cannot tell if anyone is listening.

So I will stay here for a while, between what was and what is next, trusting that this ache is not the end of the song but the bridge that leads to the next verse.

We are all in-between something. We are all tuning, listening, resetting. Wherever you are in your journey, may you find time to breathe, to notice, and to let your next melody emerge.

The Value of Embracing Square One

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Simplicity in Jazz:

In 1969, during the recording of his groundbreaking album In a Silent Way, Miles Davis famously told guitarist John McLaughlin to “play the guitar like you’re picking it up for the first time.” McLaughlin, renowned for his complex, intricate solos, was likely perplexed by this direction. Jazz, after all, is a swirl of notes, harmonies, and complexities—a musical enigma. But Miles was after something else, something new. He envisioned a sound that was simple yet profound, stripped down to its core. He wanted his band to create a fresh ambience, to tap into a deeper, purer musical experience.

This wasn’t just any jazz album. It was a collaborative effort with musicians who, for many of them, were playing together for the first time. Miles led them to embrace simplicity, allowing space for discovery. The result? An album that, decades later, still influences and inspires musicians worldwide. It stands as a testament to the power of stepping into something new with fresh eyes and an open heart.

Back to School:

For school leaders, the phrase “Back to School” stirs a similar mix of emotions: joy, anticipation, maybe even a little fear. It’s the beginning of something new, a reset button. For some, this is a welcome opportunity; for others, it can be daunting, especially for those stepping into a new school or leadership role. But there’s immense value in embracing these new beginnings, or what I call “Square One.”

Square One offers the chance to rewrite, renew, and refocus. Whether you’re a brand-new principal or a seasoned leader in a new building, starting over can feel like walking into a conversation where everyone else is already laughing at an inside joke. You may not yet be in on it, but there’s an opportunity to listen, connect, and contribute. Building trust, creating relationships, and setting the tone for a collaborative culture takes time and effort—but it’s well worth it.

As a turnaround principal, I’ve lived through this over and over. Every school, every new beginning, felt like standing at the edge of something vast and uncertain. But I’ve learned that there’s beauty in Square One. It’s where connection is made, where trust is earned, and where growth is inevitable if you lean into the discomfort.

Embracing Square One:

I used to dread the awkwardness of starting fresh. It felt like a weird dance where I would stumble more than glide. But with time, I realized that Square One isn’t something to fear. It’s a unique opportunity. In Square One, you get to build from the ground up, to create a vision, and invite others to join in shaping something beautiful for your school community. This is where you can set the stage for a culture of psychological safety, where teachers and staff feel seen, heard, and valued.

As leaders, we can choose to embrace Square One not as a setback, but as a launchpad. We get to set the tone for our schools, encouraging collaboration and creativity in ways that may not have been possible before. When we invite others to see their strengths, both tapped and untapped, we unleash the power of collective potential. It’s like that band Miles Davis assembled for In a Silent Way—everyone playing together for the first time, discovering new possibilities.

Leadership Moves to Embrace Square One:

  1. Assess the Current Reality: Work with a coach, mentor, or thought partner to clearly identify where your Square One stands. What are the challenges, and where are the opportunities?
  2. Connect with Your Community: Engage with your staff, students, and families. Share the vision for this new beginning and the path forward. Build excitement around what’s possible.
  3. Create a Roadmap: Develop a timeline with actionable next steps. Break down your vision into tangible goals. This will give you and your team a clear sense of direction.
  4. Reflect Regularly: Take time each day to journal and reflect on the progress being made. These reflections will guide future decisions and help keep you grounded in your purpose.
  5. Celebrate Wins: Don’t wait for the big milestones. Celebrate small wins along the way, and do it publicly. Acknowledging progress builds momentum and fosters a positive culture.

Conclusion:

Just as Miles Davis sought a deeper sound by stripping away the complexity, we, as school leaders, can find clarity and strength in the simplicity of Square One. Embracing the beginning allows us to reset, reimagine, and reframe the possibilities for our school communities. As we step into new roles or new school years, let’s lead with intention, vulnerability, and an openness to collaboration. The beauty of Square One lies not in its uncertainty, but in its promise. Like Miles and his band on In a Silent Way, we have the opportunity to create something timeless by being fully present in the moment.

Listen to Miles Davis’ In a Silent Way here.