This blog continues our yearlong headship series, which will explore a different aspect of headship each month.
I grew up with a stutter.
Not so severe that I couldn’t speak, but severe enough that words sometimes got stuck. I would have an idea I wanted to share but no way to get it out. In those moments, I often chose silence. I learned early that being confident in what you know and actually being able to say it are two different things.
The stutter instilled in me a humility that an otherwise successful student and athlete might not have had. I share this not as a confession but as an orientation. When I walked through the doors of Cheshire Academy (CT) in January 2025 to begin my tenure as head of school, I found myself reaching for that old, familiar lesson. I did not need to learn how to speak. I needed to find my voice.
Before Cheshire, I was the founding head of New England Innovation Academy (MA). I built something from nothing—culture, systems, community, identity. We opened our doors 14 months after I arrived, in the middle of a pandemic, with 70 students, a dozen teachers, and a founding cohort inspired by the vision and united by our shared frustration with educational inertia. I earned my credibility there, one decision at a time.
I carried that confidence into my new role, assuming, without quite knowing I was doing so, that having founded a school and having worked at nationally known boarding schools would naturally translate into credibility upon arrival. But my past experience had not prepared me for the deepest work of joining a school with hundreds of years of history: learning the rituals, stories, loyalties, and truths that were already there. You cannot prepare for this from the outside. You can only listen your way in.
What the Search Process Doesn’t Prepare You For
The search process is remarkably good at certain things. It tests your strategic thinking, your ability to articulate a vision, and your fluency in the language of institutional leadership. It asks you thoughtful questions about budget pressures and enrollment, board governance, and change management.
What it cannot prepare you for is this: the school that was here before you.
Cheshire Academy is 232 years old. It was founded in 1794 (during George Washington’s presidency) by Samuel Seabury, later a bishop and, thanks to the musical Hamilton, now a household name. The school has reinvented itself many times across its long history: Episcopal academy, military academy during the Civil War, Roxbury School modeled on the Oxbridge tutorial system as a Yale feeder, and finally Cheshire Academy in 1937. It has survived wars, recessions, pandemics, and dozens of heads of school.
That history does not live only in archives or timelines. It lives in the faculty member who has taught here for 30 years, seeing five heads come and go. In the alum who attended in the 1980s and donates every year because one teacher saved his life. In the family that has sent three siblings and expects a certain kind of welcome.
In my first months, I did what most new heads are counseled to do: I listened. I met with faculty, staff, parents, alumni, and trustees. I asked what they loved, what they feared, what they wanted. But I also learned that there is a fleeting opportunity, perhaps within the first 12 to 18 months, in which a new head has a particular kind of standing to name the truth of the moment. Wait too long and you've become part of the institutional furniture. Move too fast and you haven't earned the right to be heard. The window is narrow.
Where Courage Actually Comes From
Before I became a head of school, I think I imagined that the courage required of the role would look like the courage we associate with leadership: the bold speech, the hard call, the strategic pivot delivered from a podium.
The truth is quieter and harder.
About five months into my tenure at Cheshire, we had a fire in one of our dormitories early on a spring morning. By the time I arrived, every student was safe. The firefighters were safe. The crisis was, in the strictest sense, already over.
What came next—the communication, the logistics, the relocation, the hundreds of small decisions about clothing and housing and follow-up care—required nothing heroic. What it required was steadiness. Clarity. A willingness to reframe the moment from “catastrophe” to “problem set.” The courage of the moment was not in any grand gesture. It was in picking up the phone and calling families one by one. It was in standing in front of faculty on Zoom an hour later and being calm on purpose. It was in saying, “Here is what we know, here is what we don’t, here is what we are doing next”—and then doing it.
That moment became a kind of introduction: not to my résumé or my intentions, but to the steadiness people could expect from me when the school needed it most. Since then, I have come to believe that courage in this role is:
- rarely dramatic. It is mostly consistency under pressure—doing what you said you would do, when you said you would do it, often when no one is watching.
- being visible—in the dining hall, on the sideline, in the hallway—on your worst day, not just your best.
- being willing to be humble in public. To say “I was wrong about that” or “I don’t know yet” without dressing it up.
- not treating every problem as urgent. The real urgencies announce themselves. The instinct to act quickly can feel brave; often, it is the opposite.
What Lasts After the Strategic Plans Fade
I just finished my first full academic year and am about to present a strategic plan to my board for approval. It is the product of a year of community input synthesized into a document that is both specific and, I hope, durable. I am proud of it. I believe in it.
I also know that it is not the thing that the community will remember.
What people will remember is whether they felt heard during the planning process. Whether the faculty member who disagreed with the direction felt that her disagreement was engaged with, not dismissed. Whether the parents who showed up to the coffee chat with concerns walked away feeling more connected, not less. Whether the small gestures—the handwritten note, the hallway conversation, the name remembered, the promise kept—accumulated into something that felt, over time, like trust.
The head of school doesn’t do the core work of the school—the faculty do. My job is to coordinate, to hold people accountable, and to bring energy. I am measured by how well the people around me do their work, not by how visible I am doing mine.
The longer I sit in this role, the more I understand that trust depends on holding two truths at once: people need to feel known and cared for, and the institution still needs clarity, discipline, and direction. Schools are part family and part business. They need the warmth, belonging, and loyalty of a family but also the focus and accountability of a business. The tension between those needs never fully goes away. Leaning too far toward family risks avoiding necessary decisions in the name of care. Leaning too far toward business risks losing the very soul that makes a school worth attending. The work is holding both, every day, in the right proportions for the moment.
The Rebuilding Is the Work
If I could go back and tell the version of myself who was packing boxes for Connecticut in December 2024 one thing, it would be this: Building credibility in a new community is not a prelude to the work. It is the work.
You do not earn authority once and carry it with you for the rest of your career. You earn it in every new community, from scratch, by being who you say you are for long enough that people can see the pattern. The résumé opens the door. What happens after the door opens depends on whether you keep your promises, tell the truth when it is inconvenient, notice and thank the people whose work keeps the school running, and remain the same person at the podium as in the parking lot.
It turns out the stutter was teaching me something I would need for the rest of my life: not only that words can be hard to get out, but that voice is not a possession. It is a practice.
Every new community asks you to find it again. The courage that sustains you is the willingness to begin.
Check out Woelper’s Member Voices episode where he reflects on navigating financial pressures, fostering belonging in a diverse boarding‑day community, and shaping personalized pathways that help students thrive academically and personally.