This article appeared as "The Last Headmaster" in the Winter 2024 issue of Independent School.
I earned a “C” in his life science class 28 years ago—the same year he coached my middle school basketball team. Once he assigned me to summer school detention, which meant working with the head of facilities for eight straight, grueling hours, three days in a row. The crime: I had been disrespectful to a teacher, and when she sent me to his office and I found it empty, I left. It was field day, and I could not miss field day. Countless times he asked me to tuck my shirt in, shave, get a haircut. He sent me home one day for wearing an inappropriate T-shirt to school. He was an anchor of discipline in the tumultuous sea of adolescence.
He is Fred Moulton, the last headmaster. I call him this because over time, I’ve observed a critical distance between leaders and their schools. We are now “heads of school,” a term that feels less emotionally invested, more technical. The role has shifted further toward public relations and fundraising, all in the name of competition and keeping the machine running. We are stretched thin by myriad responsibilities, so we are delegating leadership on teaching and learning, culture, and wellness; the distance between leaders and their students and teachers extends. Schools today are seen as places to be managed, not led. I get the sense that the idea of spending a career in one place is antiquated, and we are comfortable being the 14th head of school as opposed to leaving an enduring legacy.
For 38 years, Moulton led Wilson Hall (SC), doubled its size and swelled its academic reputation, developed its facilities and solidified its traditions. No one could imagine the school without him, but this past year, they had to because at graduation last year, he passed me the headmaster’s baton and began his retirement. The baton could have been a torch, since the year in which I shadowed Moulton was my training for how to “carry the fire” forward, as Cormac McCarthy coined in The Road.
Keeping the fire burning for nearly four decades was an Olympic feat. Moulton diligently led through so many impactful social and societal shifts and events—from the Challenger explosion in 1986, through the AIDS epidemic and the fall of the Berlin wall, to the Columbine shootings and the Great Recession, to the Black Lives Matter movement and the COVID-19 pandemic—the impacts of which still reverberate today. (And offer lessons for the leaders, like me, wrestling with similar shifts.)
Board members wanted him fired, parents petitioned against his decisions, and students turfed and rolled his yard on multiple occasions. But Moulton led with conscience, intuition, and conviction. He held the tension between traditional and progressive. He was never a purist because he understood the danger of absolute certainty.
I shadowed Moulton during the past academic school year, and now, as I am in my first year as the head of school, I recognize the blessing it has been to witness a different quest, the one of the last headmaster. The lessons he imparted are simple, really. And simplicity, married to great love and discipline, was Moulton’s formula.
A Drive to Understand
A year-long transition is an incredible privilege, a gift of timing and the financial ability to pay two heads, and if it’s possible, schools should take this option. I observed, I listened, I reflected: Why does this rule exist? Why does this process have so many steps, or so few? There was absolutely no pressure to perform, to do anything but learn. Of course, I wanted to, like when I discovered we didn’t have a school credit card. I thought, “Well, here’s low-hanging fruit; next year, add a school credit card. It will make life much easier. Check.” An easy win, but ultimately, I was ignorant of why this decision had been made and arrogant to think my solution was somehow novel—had no one but me thought a credit card might be a nice convenience? Moulton said, “Just watch.” So, I did.
We were more careful with money. Why? Because the reimbursement process was an inconvenient prospect, a deterrent that prevented teachers and staff, me included, from making flippant decisions with the school’s money. Convenience always lightens the conscience, and psychologically, there is something a little different about spending your money first. More caution. But even better, if they had to put purchases on their credit cards, people enjoyed earning extra points for flights, cash back, or Amazon points.
I may still make the decision to add a school credit card, but now the decision will be made differently. For a year, Moulton asked me to embrace the paradox of “Chesterton’s Fence,” a simple rule that suggests you shouldn’t destroy a fence—or change a rule—if you don’t understand why it was created in the first place.
I will have a better understanding of why the fence was erected before removing the fence. Too often, leaders join a new educational ecosystem and, under the pressure of “leadership,” rip fences out of the ground and call it “innovation” or “improvement.” But innovation and improvement don’t begin with purgation. They begin with understanding.
Embedding Wisdom
To carry the fire, as the last headmaster did, one must be a gardener, not a maximizer. And that means a slower pace, more gratitude and meaningful conversations, a human-centered approach, not a goal-centered one: Those are the nutrients required for a healthy educational system.
Moulton never hired out what he knew needed to be emergent. If students were unwell and isolated, he didn’t start new programs or add curricula or hire new directors; he reminded the community of its values. If health, nor love of learning or human decency, didn’t emerge from the system, he redirected the community’s focus back to the mission, reminded teachers of their agency and responsibility in the developmental process, and asked how he could help. He knew that adding complexity to an already-stressed system is never the answer.
Moulton reminded me last year that without embedding wisdom into our systems, our systems will run amok. Wisdom is law, wisdom is restraint and patience, wisdom is what prevents us from pursuing narrow goals, wisdom is seeing the whole and not just the parts. In small ways he demonstrated this principle, like the way he limited his daily appointments to one or two meetings. Moulton’s concern was not efficiency; it was impact. He knew that a frantic headmaster compromised his own discernment. In big ways he demonstrated this principle, too, like the way he refused to recruit athletes to support the narrow goal of winning at all costs. Instead, his athletic programs focused on player development, and some years were successful, some were not. Or how, under his leadership, the school did not balloon into a buffet of programs, the be-everything-to-all-people approach so many independent schools take. Staying lean and mission-focused, he was committed for the long term.
But all great quests claim the hero’s life—and “claim” does not always mean a physical death, though it’s often included. No, claim means more of a spiritual death, a complete sacrifice for something greater than yourself. And it has been no different for Fred Moulton—his quest has claimed his life. For those who demand work-life balance, you will never understand a man like the last headmaster; in fact, he may upset you. What we have forgotten—and must recover—is that carrying the fire warms everything and everyone around us. It is a joyous sacrifice.
I leave you with a final image: Walking with a cane one month after a minor stroke he suffered last January, the last headmaster bends his 6-foot-4-inch frame and picks up trash in a courtyard near the gym, a wandering napkin escaping from the picnic tables under an old oak tree that, though nearing death, still provides shade in the warm days of spring. To let that napkin go would violate everything Fred Moulton stood for, and if you understand that, you understand the last headmaster.
