In the later years, the work turns inward and outward at once. The focus shifts from momentum to meaning, from building to tending. Leaders are thinking less about what comes next and more about what endures.
This article appeared as "The Best Parts of the Job” in the Summer 2026 issue of Independent School.
In January, I was having a rough week—by which I mean a week that would feel rough to anyone, head of school or not. We were on the long march from Christmas to spring break. A new faculty member had resigned unexpectedly, and not for any good reason. Every day, the sky pressed down, heavy and gray. It was cold. Worst of all for us school people, it only snowed on Saturdays. Two newly diagnosed bulging discs were my constant companions.
Near the end of one day, as I climbed the stairs to my office, I heard a student call out, “Mr. Byrnes!” Uh oh. I stopped on the landing as the senior hustled up to meet me. After a brief exchange, he looked me in the eye and asked if I remembered why we had expelled him as a freshman. I couldn’t help but chuckle (we don’t expel a lot of kids) and said that I did. He smiled and said, “I just wanted to thank you for letting me come back. You changed my life.” A little dumbstruck, I reminded him that he had done the hard work. “I just wanted to be sure that I told you that,” he said, shook my hand, and headed back down the stairs.
The independent school headship is an occupation, or more accurately an avocation, very much informed by signs from the universe. When we’re open to receiving them, those signs can guide our decisions and affirm the goodness of what we try to do. I embraced that one gratefully. I was filled with gratitude—excitement even—though times were still a bit tough.
Acknowledging forces larger than ourselves is part of cultivating what researcher and psychologist Lisa Miller calls an “awakened brain.” In her book The Awakened Brain, Miller says that one key to managing the complexity of life is through recognizing synchronicity, or “when two apparently disparate events are joined at the level of meaning or consciousness,” which is “an accessible way to illuminate and validate those sparks of inner knowing, those flashes of meaning or insight that seem to arrive out of the blue.” I’ve come to see this awareness as integral to my success and happiness in the work. On that day on those stairs, the message was clear: Keep going. Don’t lose sight of the good. Cherish the relationships that sustain you.
Once you are open to seeing them, the signs tend to proliferate. They can lift you up and pierce the fog of ambiguity through which heads are frequently required to wander. The gravity of the job and the responsibility of leading an institution that changes young lives can create inertia and weight, but attending to the good—to the daily miracles—can lift us up and move us forward.
Changing the Narrative
What happens when we don’t see the signs—when we only focus on problems and disappointments, when hard things are just hard things and never doorways to new understanding or small wins along the way? When does the prevailing narrative become that the job is simply too damn hard?
Well, the job is damn hard. Heads are asked to do too much, and to be too much. We’re expected, often simultaneously, to solve the problems of students, parents, the school, the board, even society itself, without much help. It’s no wonder that while many are called, fewer find ways to flourish and keep going.
But many do keep going because they believe that the challenges—the job’s unrelenting difficulties—are precisely what make the headship just the thing that leaders need. That is a narrative that we don’t hear often enough. Successful heads learn to reframe the experiences through the lenses of leadership, learning, and human development. They are always learning. They awaken to the good, and they can live the headship as the unique and powerful leadership experience it is. The best heads develop these dispositions with discipline and intention. They learn to see where things are going because they’ve been there before. And they don’t go anywhere without a sense of humor.
Noticing when a challenge turns into a win is one key to thriving. Do we notice the energy generated by a particularly effective meeting? The satisfaction when a school event shows our students at their best, or when data confirm the success of a program that has been evolving over time? That one-minute, animated, unsolicited conversation with the junior who couldn’t even look at you as a freshman? The quiet pride of managing a budget into the black, especially in challenging times? The more that I look for the signs of goodness and reward in my work, the more I see. If we dwell on the difficulties and focus only on how hard the job is, we miss the frequent and essential goodness of it all.
I often joke that people love to talk to me at parties—not because I’m funny but because I’ve got the most interesting job. Navigating an unexpected resignation. Landing parental helicopters. Planking at a fundraiser. Writing an AI proposal that could change the trajectory of the school’s future. Watching young people learn to thrive as good humans. Who else gets to do this and get paid? It is a lot—sometimes in one week—but for those who aspire to lead, and want to do so in what is arguably the most relationship-based and human-centric profession in the world, these are the experiences that should keep us coming back. We just need to let them.
It is sometimes astonishing to me that despite the obvious difficulties of the job and the dire narratives surrounding it, we have so many effective, tough, caring, intellectually and emotionally intelligent people leading our independent schools. Many of them would thrive as leaders in almost any other occupational context. Some actually have. So maybe we can work on the narrative a bit. Maybe there are sane people who not only survive but thrive in this job.
It’s no surprise that younger leaders hesitate to consider headship amid a culture saturated with burnout stories. For them, I offer a counter-narrative—one that allows successful heads to live, comfortably most of the time, with the hard stuff. These are some of the reasons to consider such a powerful and sustaining calling.
Lifelong learning. In headship, learning is essential to thriving—and even surviving. Formal learning—new research in the science of learning, the art of management, navigating profit and loss statements, asking for money—is integral to the work, but so is introspection and self-discovery. Today’s heads inevitably become experts in human development: their own, their faculties’, and, most important, their students’. Just as critical is learning to recognize and tend to one’s own emotional and spiritual health. A somewhat ironic benefit is becoming a more balanced, healthier, and happier human by learning to thrive in the chaos of school leadership.
Relationships that last forever. While the healthy development of children is the north star, great heads understand that the adults who help enact that vision must also be healthy and flourishing. Heads are, above all, human-relators—finding ways to nurture faculty and staff and, at times, parents by cultivating purpose, belonging, and care within the school’s adult community. Strategic heads develop strong leaders within their institutions and are grateful when some go on to lead other schools. Wise heads also cultivate friendships with fellow heads—networks of fellow travelers from whom they can learn and with whom they can commiserate and share wisdom.
Enacting a shared vision. Thriving heads hold a vision for education and human development that sits at the heart of everything they do. They believe deeply in the necessity and power of school and remain curious learners, continually refining their understanding of what works best for young people. Their vision is personal and shaped by science, experience, and intuition, and it deepens over time. All good heads are also evangelists, seeking to cultivate their belief in others.
Being courageous for a living. Heads are naturally courageous people, each in a way that fits their own personality and temperament, otherwise known as leadership style. The courage most often appears when they are asked to accept conditions that would diminish healthy human development or when they see a better path that others have yet to recognize. Heads are also stretched to their limits by the most dire of circumstances—a death in the community, abuse of a child, a pandemic—but they recognize these moments for what they are: the great challenges of leadership.
Lack of boredom. Heads are challenge-seekers who thrive on the unpredictable and often nonstandard events and interactions that inhabit their worlds. Along the way, many learn practices—for me, meditation—that help them embrace each day and take responsibility for their own fulfillment. This is not to say that heads enjoy conflict, but they do become adept at preventing it when possible and managing it when necessary. Problem-solving is in their DNA.
Loving the Challenge
Finally, strong heads know their own value to the institution. They ask for what they need—fair compensation, rest, and autonomy—and attend carefully to their emotional and mental health. They are fierce protectors of the personal relationships that ground their work. They prize honesty, integrity, and loyalty. Heads who are successful in this aspect of the work tend to stick around. Enacting a shared vision, cultivating strong relationships, and mentoring other leaders binds them to their school in ways that make leaving harder—and staying more meaningful. Many come to realize that the place where they are, and the people they are with, give back as much meaning and support as they offer in return. Why go anywhere else?
Heads who live into these advantages are all around us. My anecdotal research tells me that they outnumber the heads who self-report that they are on fire, but we all love to hear about a good tragedy, so burnout feels more present. Through my work with regional and national head networks, I’ve had the privilege of learning from and befriending more successful, thriving heads than I can count. We are all different in how we do the work, but we share an understanding of its difficulty, its sacrifices, and its demands. We also share a love for it—complaints and all. In our own ways, each of us is a thriving leader, and none of us would have it any other way.
Read More
Explore more reflections on longtime headship:
“Leadership Lessons: Won’t You Stay Just a Little Bit Longer?” by Robert Kosasky and Amy McNamer, Spring 2024
“Leadership Lessons: A Longtime Head Reflects on School Culture,” by Paul Druzinsky, Summer 2024
“Open Door: Sustaining Leaders and Our Schools,” by Debra P. Wilson, Winter 2025