By midcareer, the work shifts. Leaders are no longer learning the role so much as living inside it, balancing momentum with sustainability, conviction with humility. They lead from a steadier but maybe more demanding middle ground.
This article appeared as "Finding Stewardship in Subtraction” in the Summer 2026 issue of Independent School.
Six months into my first headship, I stood before my faculty and staff to announce that our high school was closing. It wasn’t a sudden collapse but the quiet, grinding reality of a small, tuition-driven school where the numbers no longer worked. Enrollment was a leak we couldn’t plug, and the financial strain had become a weight the rest of the institution could no longer carry. Standing beside my board chair, I told a room of educators who had given years to these students that their division would not exist by the following fall.
In that moment, I understood what every leadership seminar, graduate course, and well-meaning mentor had failed to articulate: You are not hired to be a visionary. You are hired to be a steward. And sometimes, stewardship looks like a minus sign.
It was the moment I stopped looking for the right answers and started looking for the honest ones.
I started my first headship at Abiqua School (OR) during the summer of 2022. After nearly 25 years in independent schools—as a teacher, dean, and associate head—I came with experience, confidence, and a vision. I was eager to prove that even though I was a first-time head, I could help this small-city school thrive. I told the hiring committee I could help grow Abiqua. But “vision” is a seductive word in our industry.
In the early years of headship, it can easily become a mask for ego. We want to be leaders who add—the ones who cut the ribbon on a new lab, launch a global studies initiative, or expand the campus. Addition feels like progress; subtraction feels like a confession of inadequacy.
In a small city, this instinct to prove your worth is amplified. You don’t just lead from an office; you lead in the grocery store aisles, balancing a box of cookies while talking with a student and her parents. You lead on the Little League fields, sometimes as your students’ coach. As head of school in a community this size, you are the keeper of the brand 24 hours a day.
What I quickly learned, however, is that a school cannot survive on vision alone if it lacks coherence in alignment of mission, enrollment, finances, and culture. It is the unglamorous work of ensuring that what we say we are matches what we can afford to be.
An Act of Protection
In independent schools, we often treat “courage” as a synonym for bold expansion. But the most profound courage I have seen in headship is the willingness to admit when an institution is stretched too thin. At Abiqua, we were trying to be everything to everyone, sustaining a high school program with resources that were becoming dangerously worn. Closing that division wasn’t an admission of failure; it was an act of protection, preserving the heart of the school: our preschool through eighth grade program.
Choosing to close the high school was an act of accountability to our long-term sustainability and an expression of honor toward the mission we could actually fulfill. It required a level of teamwork the board and I hadn’t yet experienced and a shared understanding that to save the whole, we had to let go of a part.
There is a particular silence that follows a hard decision. In the weeks after the announcement, the atmosphere was heavy. There was no “leadership hack” for the conflict that followed. Some in the community had seen the decision coming for years and were quietly, almost guiltily, relieved that someone had finally said the quiet part out loud.
Others were understandably angry. There is a deep, jagged pain in telling a teacher that the program they built with their own hands will no longer exist, or in telling a family that the future they imagined for their child has vanished. There is no easy way to ask a student to find a new school midway through high school.
During those months, I learned that empathy and respect in headship aren’t about making everyone happy. They are about the willingness to sit with that anger and grief without getting defensive, to look someone in the eye and acknowledge the cost of the decision. Clarity does not eliminate pain, but it does provide a floor.
What Matters Most
Early in my career as a teacher, I asked students to look past the surface of a text and uncover its underlying structure. Now, I do the same with my parents and staff (with the good fortune of a board that already understands this). I ask them to look past the surface of “prestige” and focus on the reality of “margin.”
In a small city, the head must be a constant educator on the economics of the independent school model. It is a never-ending seminar. You have to explain, with radical transparency, that tuition does not cover the full cost of the experience and demonstrate why fundraising is not an “optional extra” but the oxygen that keeps the mission alive.
Sustainability requires realism. It requires a head who can manage the school’s “relational fabric” without becoming defensive. In a small town, a conflict with one family sends ripples through the entire pond. Grief, anxiety, and conflict aren’t managed by avoidance but by containment. You become the vessel for the community’s fears and must learn how to carry that weight without letting it crush your own spirit.
I have been fortunate to serve a board that understands headship as a practice of continuous learning, not a state of arrival. They identified my gaps early and met them not with judgment but with investment, offering guidance, strengthening thin areas, and giving me room to grow. In a small school, the most dangerous posture a head can take is infallibility. By asking questions and admitting what I didn’t know, I allowed the board and my team to become true partners in the school’s success.
Over time, the internal journey has mattered more than the external one. I have moved from trying to prove my competence to trying to protect what matters most: the culture of the faculty room, the financial health of the institution, and the “known-ness” of each child.
If you look at the arc of headship, the early years are about building capital. The middle years are about spending it on what matters. And the later years are about realizing that the capital was never yours to begin with—it belongs to the institution.
Doing the Work
When my wife, children, and I were driving across the country from Pennsylvania to Oregon during the summer of 2022 in a moving truck packed to the brim with everything we owned, we were heading west toward an uncertain future. I remember the feeling of a permanent excursion, the sense that the rest of my life was beginning at every mile marker.
Headship feels like that drive. You pack the essentials (your values, your empathy, and your resilience), along with the last-minute randoms: the unexpected crises, sudden financial shifts, the parent who shows up without an appointment. You may have the destination mapped out, but a new challenge appears around every bend in the road.
Strategic plans eventually gather dust. New buildings grow old. Crises that once felt existential are barely remembered a few years later. What lasts is culture. What lasts is trust.
I have learned to let go of the need for universal approval. In my first year, a critical email from a parent could ruin an entire weekend; it felt like a personal indictment. Now, I see conflict as a data point, a signal of where the “coherence” is beginning to break down.
I confidently move between the micro and the macro. In the span of an hour, I meet with the school’s attorney, and I help a student find a lost shoe; I move from a high-stakes board discussion about facilities to the playground, where a student wants to tell me a very long story about a ladybug. I’ve learned to be human in both spaces: the head who understands the audit and the head who knows which teacher’s parent is in the hospital.
And at Abiqua, the consistent, quiet work has led to enrollment growth. Families who hesitated to join a school that felt unsettled or stretched too thin began to see a leadership team and board willing to face reality. We stopped trying to be a “prestigious” high school and started being a coherent preschool to eighth grade. We traded a wide, shallow vision for a narrow, deep mission.
I often think about hope in education: the idea that we are planting trees whose shade we will never enjoy. That is the ultimate truth of headship. You work for a future you may never see, building something for students who will graduate and forget your name, and that is exactly as it should be.
An Act of Faith
For those aspiring to headship, my advice is simple: Stop trying to be the hero of the story. Be the steward of the mission. Don’t overestimate the power of your vision, and don’t underestimate the power of your presence—in the halls, at the games, and in difficult meetings—it’s your most valuable currency.
Courage doesn’t always roar. Sometimes, it’s the quiet voice at the end of a long day that says, We will try again tomorrow, with more clarity than we had today.
I am still a head of school in a small city, still navigating the complex economics of independent schooling. But I no longer measure success by what I have added to the school. I measure it by the coherence I have helped create. I have stopped trying to prove that I can do everything, and I am now content to protect what matters most: the trust of my faculty and community, the stability of our future, and the simple, human moments when a child feels seen.
In the end, headship is an act of faith, an accumulation of lived moments, some painful and some joyful. It is the work of keeping the heart of the school beating, even when the rhythm has to change.