Typically, I don’t write blog posts back-to-back. I’ve kept to a steady rhythm of weekly writing since my heart episode last year. That ritual has become part of my healing—recommended by my therapist, yes, but also something I’ve come to cherish. Writing has broken through the fog of writer’s block that followed the release of The Pepper Effect. Through journaling and reflection, I’ve found my way back to words and meaning. I am even working on finishing up a proposal for a new book.

But this piece couldn’t wait.

I’ve been sitting with a question no one prepared me for in “Principal School”:
Why does leadership have to feel so lonely?

It’s a question that’s erupted into big feelings—enough to make me pause on other writing projects and sit with this one instead.

There’s a scene in Peter Jackson’s Get Back documentary that lingers with me. George has left the band. A meeting doesn’t go well. Paul and Ringo return to the studio, uncertain of what’s next. John is nowhere to be found. Paul, visibly shaken, says quietly, “And then there were two.” He stares off into the distance. His eyes well with tears. His voice trembles. You can feel the grief. The possibility that something beautiful and world-changing might be coming to an end.

Watching that moment recently, I didn’t just see it through the eyes of a Beatles fan—I saw it through the lens of a leader holding onto connection, trying not to lose grip.

I’ve been a principal for almost sixteen years. I’ve served in multiple schools, answered the call for turnaround, and poured myself into the gig. I’m grateful for a beautiful family—my wife and three amazing daughters. Their love is a constant light. And I do have a handful of trusted friends, most not nearby. But I’ve felt friendship fade over the years—some lost to distance, some to time, some to disillusionment.

This is the part they don’t tell you about leadership. That people may see your title before they see you. That the weight of tough decisions can sometimes isolate you. That you’ll have days where it feels like everyone is counting on you—and no one is standing with you.

I once thought the PLN (Professional Learning Network) would solve this. Twitter, Voxer groups, hashtags that I created like #CelebrateMonday and #TrendThePositive—those were my entry points to community. And for a while, they worked. I met incredible educators, interviewed inspirational guests for the Principal Liner Notes podcast, and even achieved my dream of becoming a published author.

But not all connections held. Some collaborations quietly ended. Some people I looked up to didn’t turn out to be who I thought they were. And yes, I’ve even had a book idea stolen.

Still, I’m thankful for the moments of light in those spaces—moments when a shoutout brightened someone’s Monday or a podcast guest became a kindred spirit. Yet, after the episode ended or the tweet was sent, the silence would sometimes creep in.

Loneliness doesn’t negate purpose. It doesn’t mean the work isn’t good. But it does mean we need to be mindful of our well-being and human need for belonging.

Recently, I’ve had the privilege of co-facilitating the ISTE-ASCD webinar series with Andrea Trudeau. We’ve explored what it means to create spaces of connection and belonging—especially for those in unique roles like principals and school librarians. These conversations have reminded me that belonging doesn’t just happen. It’s a practice. A choice. A rhythm to keep playing, even when the band seems scattered.

In her book The Let Them Theory, Mel Robbins has a powerful chapter on the quiet heartbreak of adult friendships. She describes how friendships shift from group experiences to individual efforts—and how easy it is to look around one day and realize your circle has vanished. Her advice? Reach out first. Be kind without expectation. Smile. Be curious. Give it time.

It’s advice I’ve tried to follow, even when it’s hard. Even when it’s lonely.

So what do we do with this?

We remember that our core matters. Our heart matters. And so does connection.

Here are a few ways I’m working to move through leadership loneliness—and maybe they’ll help you, too:

• Savor family and those who know you beyond your title. The gig will wait—those moments with loved ones won’t. I am grateful daily for my wife and our daughters and my family.
• Reach out. A coffee, a text, a hallway chat. Don’t wait for someone else to go first.
• Find “only ones” like you. Look for the school librarian, the instructional coach, the counselor—others who might be the only one in their role. Forge that bond.
• Be vulnerable. Share your story. Someone else might need to hear it. I have been writing deeply about the experiences surrounding my heart episode. I am grateful that others have found it helpful for their journey.
• Build something outside the gig. A book club. A podcast. A project that brings joy without the pressure.

You are not alone—even when it feels that way. Someone out there gets it. Someone is looking for connection, too.

Keep showing up. Keep being kind. Keep playing your part in this great, imperfect, meaningful symphony of leadership.

Postscript:
During those Get Back sessions, Paul’s loneliness was palpable. But the story didn’t end there. The band found their way back. The Beatles regrouped. And they gave us the Rooftop Concert—a final live performance filled with joy, grit, and unity.

It was their last time playing live together. And it was iconic.

A reminder that even in moments of disconnection, something timeless can still emerge.