Principal Leadership

Hold On to Your People: A Note for School Leaders (and Myself)

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They don’t tell you in principal school just how lonely this gig can be.

Sure, there’s training on instructional leadership, school law, strategic planning, and evaluation protocols. All important stuff. But no one pulls you aside and says, Hey, just so you know, this work will sometimes feel like you’re on an island. Even when you’re surrounded by people, it may feel like no one sees the real you.

This is something I’ve carried with me in all my years as a principal.

Maybe it’s the pace. Maybe it’s the weight of making sure every child is seen, every adult is supported, and every decision aligns with the mission. Or maybe it’s just that in the whirlwind of trying to show up for everyone else, I started to drift from those who know me best.

I’ve lost friends. Not from fights. Not from falling outs. Just from the slow fade that happens when the job becomes the only song you play. And I’m learning through therapy, reflection, and some long walks with myself that it doesn’t have to be that way.

This summer reminded me.

At the ISTE-ASCD Conference in San Antonio, I was surrounded by kindred spirits. Educators, innovators, and thought partners I’ve known for years through screens and conversations. We laughed. We shared. We learned together. But most importantly, I wasn’t “Principal Gaillard.” I was just Sean. The same Sean who loves vinyl records and The Beatles. The same Sean who shows up with a notepad full of scribbles and a heart full of ideas. That feeling of being seen and embraced without the title attached nourished something in me.

That same feeling showed up again in a different space at my cousin’s wedding in Michigan. No one was asking for school updates or strategic plans. I was simply a cousin. A brother. A nephew. A dad. A husband. I was known not because of what I do, but because of who I am. Nothing will beat the joyful moment of hitting the dance floor at the wedding repection with my wife and daughters.

Those moments sustained me. And they reminded me that who I am matters just as much as what I do. Maybe more.

So this post isn’t just a message for my fellow school leaders as we enter another school year. It’s a note to myself.

Don’t lose your people.

The ones who love you for your corny jokes. The ones who know your favorite song. The ones who don’t care about your school data but care deeply about your heart.

Leadership doesn’t have to be lonely. But we have to choose connection on purpose. That’s the work I’m trying to do. And if it helps, here are four small, doable moves I’m committing to this year. Maybe they’ll work for you too.

4 Moves to Stay Connected (That Even a Busy School Leader Can Do):

1. Send one text a week to a friend.
Not a long update. Just a quick check-in. Thinking of you. Hope you’re good. It takes less than a minute but can mean everything.

2. Put a standing “non-school” date on your calendar.
Maybe it’s coffee with a college friend once a month. Maybe it’s a walk with your partner every Thursday evening. Block the time like it’s a meeting. Because it is a meeting with the best parts of yourself.

3. Say “yes” to one invite.
Even when you’re tired. Even when the to-do list is yelling. If a friend invites you to dinner, a concert, a call—say yes. One yes can reconnect you to who you are outside of the principal’s office.

4. Name your people.
Make a list of 3 to 5 folks who know you beyond the job. Tape it to your desk. These are your people. When the days get heavy, look at those names. Then call one. Or just remember their laughter. That’s your reset button.

As this new school year begins, don’t forget the people who walk with you outside of the school walls. They’re the ones who keep your heart steady. They’re the ones who remind you that being just you is more than enough.

I’m holding onto my people this year.

Hold onto yours.

The Rooftop Moment: Embracing Creative Courage Amidst Doubt

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I’ve written and rewritten this blog post countless times in my mind. It has been weighing on my heart, especially after navigating a week filled with a few setbacks. Nothing catastrophic, but still moments of dejection that linger. One of those moments was particularly difficult: an idea I had for a collaborative book was taken in a new direction—without me.

As someone who values collaboration and the joy it brings, I’ve learned that I need to be more mindful of whom I choose to collaborate with. Seeing my work and ideas rebranded as someone else’s originality hurt deeply. It stung because the creative journey is already fraught with battles against Imposter Syndrome and anxiety. These emotions creep in especially when I venture into new creative territory: Will it be good enough? Will people understand what I’m trying to do? When someone else quickly disinvites you from a project and takes it solo, it’s a painful reminder of the delicate steps needed to protect your own creative vision.

Late last year, I thought I had cracked the code on a follow-up to my first book, The Pepper Effect. I had an outline, a vision, and an unshakable drive. But that momentum fizzled as life threw its challenges my way. Stress, high blood pressure, and self-doubt culminated in a health scare that landed me in the hospital. It was a wake-up call. With the support of my incredible wife, my family, my therapist, and my faith, I began to rebuild—both physically and emotionally. Part of that rebuilding process involved reconnecting with my writing. Blogging weekly became my creative anchor, a way to keep my writing muscles intact and grooving. Each blog post has been a step forward, a way to regain confidence and prepare myself for the marathon of writing another book.

The recent letdown with the collaborative book idea is a chapter I’m reframing not as failure, but as a lesson learned. It’s a reminder to trust my vision, something I wrote about extensively in The Pepper Effect. Sure, it stings to see accolades being given for an idea that I helped shape, but as Mel Robbins writes in The Let Them Theory, I can’t let other people’s actions control my journey. Let them take their version of the idea, I tell myself. Let me move forward with my vision. And as my therapist often reminds me, “…and that’s okay.”

When I need inspiration, I return to The Beatles. They are my creative North Star. My first book explored how their story is a template for creativity, collaboration, and innovation. My follow-up book, which I’m calling The Let It Be Effect, will continue in that vein, diving into the Get Back/Let It Be era. If you’ve followed me on social media, read my blogs, or listened to my podcasts, you’ve seen glimpses of this concept. The Let It Be Effect will build on the four tenets of The Pepper Effect (Believe in your vision, Believe in your masterpiece, Believe in your collaborators, Ignore the Naysayers), but it will also introduce something new: the idea of the Rooftop Moment.

The Rooftop Moment is inspired by the Beatles’ legendary final live performance in January 1969. During the recording of what would become the Let It Be album, the band faced immense challenges. They hadn’t performed live in three years, there were creative differences, and at one point, George Harrison even quit the band. Despite all this, they decided to perform—not in a grand concert hall, but on the rooftop of their Apple Corps headquarters in London. It was a cold January day, and the decision to perform wasn’t finalized until the last minute. According to director Michael Lindsay-Hogg, John Lennon’s decisive words were, “F— it—let’s go do it.”

And they did. The Beatles, joined by keyboardist Billy Preston, walked up to the rooftop and made history. That performance became their iconic Rooftop Concert, a moment of creative triumph amidst doubt and adversity. It was the final time they performed live together, and it remains a testament to the power of taking bold action despite uncertainty.

The Rooftop Moment is about just that: taking a dynamic leap of creative courage when the odds feel overwhelming. It’s about playing your gig, painting your masterpiece, or writing your book, even when doubt tries to hold you back. The Beatles ignored convention and their own self-doubts to create something unforgettable. I know I need to do the same with my follow-up book.

Let the critics and naysayers have their opinions. Let them. As for me, I’ll aim for my Rooftop Moment—that decisive act of putting my creativity into the world, no matter what. I’ll let the inspiration flow and trust that what I create will resonate with those who need it most. And that’s okay.

I hope this inspires you to find your own Rooftop Moment. Whether it’s a project you’ve been hesitant to start, a challenge you’re ready to face, or a dream you’ve been quietly nurturing, remember: the world is waiting for your masterpiece. Let it be.

Four Moves to Create Your Rooftop Moment:

  1. Lead with Vulnerability: Share your passion or a creative idea with your team or community, even if it feels risky. Vulnerability fosters connection and courage. For me, this was bringing my guitar to school and sharing a song I wrote based on our school’s core values during grade-level assemblies. It was risky, but it created a memorable and inspiring moment for my students and staff.
  2. Model Risk-Taking: Show your team that it’s okay to step outside their comfort zones by doing it yourself. Whether it’s trying a new teaching strategy or presenting an innovative idea, your example can inspire others to embrace risks.
  3. Create Space for Creativity: Provide opportunities for your staff and students to experiment and express their ideas. This could be through collaborative brainstorming sessions, innovation labs, or simply encouraging them to bring their unique talents to the table.
  4. Celebrate the Journey: Acknowledge the effort and courage it takes to create something new, even if the outcome isn’t perfect. Recognizing progress builds momentum and reinforces the value of the creative process.

Sometimes you have to aim for what I call that Rooftop Moment—that moment where you take a move for dynamic creative action amidst overwhelming odds and you simply play your gig, paint your masterpiece, write your book. The Beatles ignored convention and their own self-doubts and applied the Let Them theory in their own way. I know I have to do the same in writing my book follow-up because I know I have another book in me and that’s ok.