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 "To Hold and Be Held” in the Summer 2026 issue of Independent School.
Year 1
In Year 1 of my headship, 2020, I met my community through a screen. I arrived with plans for a structured listening campaign—intentional, gradual, designed to build trust and earn my place. Within weeks, when a pandemic shut down the world, that plan gave way to something none of us had trained for. I gave out my personal cellphone number to employees, families, and board members. The line between personal and professional dissolved almost overnight. I co-led a COVID task force with physicians, parents, and trustees; convened Bay Area heads; collaborated with county health officials—and did it all while still in the process of learning people’s names.
That year at St. Paul’s Episcopal School (CA) taught me something I couldn’t have learned any other way: Headship, at its core, is about showing up for people in conditions you didn’t choose. Each of the years that followed would ask me to relearn this lesson—under different pressures, with different stakes, and with more of myself.
Year 2: The Loss That Let Me In
Still navigating COVID-19 protocols and the long emotional tail of the pandemic, I lost my mother—my closest friend, my most honest adviser, the person who knew me best—to cancer. The loss was seismic. It cracked me open in the middle of a school year, in a community I was still becoming part of.
What I didn’t expect was what that grief gave me: entry. Suddenly I belonged to a quiet tribe within the school—parents, teachers, staff who had also lost someone essential. They found me. They offered hugs I didn’t deflect. I let myself be held by the community I was supposed to be holding. There’s no manual for that kind of reciprocity, and I’m not sure I would have believed it was possible before it happened.
That year, I learned that being human is not a liability in this role. It is the work.
Year 3: Stride, Then Stillness
The summer before Year 3, we held my mother’s memorial in Taos, New Mexico—a place she loved deeply, where she had her primary art studio and the home she and my father had built together. There was something clarifying about that ritual. Grief had been formless for a year; the memorial gave it a shape. I came into the school year having honored her, which is different from still being in free fall.
That fall, my assistant and I joined a local boxing gym, going during lunch breaks. I had always wanted to try it, and the combination of the physicality, the discipline, the doing-it-with-someone was exactly the right medicine. I was getting strong again. Sleeping. Showing up fully. By midyear, our team felt the same shift. The strategic planning process we had launched was moving with real momentum—tight, well-designed, authentically ours. I was serving on two outside boards and, for the first time, felt genuine capacity to offer beyond my own school. Mentally, physically, professionally, I was present in a way I hadn’t been.
Then, the diagnosis came without warning. No symptoms—just routine bloodwork, atypical results, a follow-up, and then the words that stop the world. I felt healthy, strong, fully engaged—and cancer arrived anyway.
What came with it, unexpectedly, was a new layer of grief for my mother. Her own cancer journey had been isolating in ways I hadn’t fully understood while I was caregiving and then mourning. Now I knew it from the inside: the fear, the uncertainty, the strange suspension of ordinary life. I carried both things at once—my own diagnosis and a belated reckoning with what she had carried alone.
My team had to coalesce faster than any team should. There is a particular kind of trust that only gets built in the fire. They found it.
Year 4: Coming Home to a Different Room
Through treatment and into recovery, my family carried me. That is not a figure of speech. They were the ones who made it possible to keep going—present in ways the institution could not be, holding the private self that the professional role never fully sees. I set goals that had nothing to do with school: to be well enough to watch my daughter perform at the Hollywood Bowl and in Central Park that summer, her voice carrying across those stages while I sat in the audience still in treatment, still fighting.
And then, in Year 4, to stand with my father at my son’s graduation from Pratt Institute—my father, who had lost his partner and was now watching his grandson step into his own life. We were all there, together. Those moments were what recovery was for.
At the same time, the school was being held by people who rose to the occasion in ways I will never stop being grateful for. My two board co-chairs stepped up during my leave—covering community events, communicating to families, steadying the team. They understood that their presence wasn’t just governance; it was a message to the community that the institution was whole even when its head was not.
I worked remotely for more than half the year, and my administrative team redistributed responsibilities without bringing in an interim head. Then the admissions and programs directors both went on medical leaves of their own. We became a community of people covering for each other through different seasons of need—which I’ve come to believe is one of the most honest expressions of who St. Paul’s is.
My first day back in person was during the third week of February. I walked in bald, visibly returning from something physically hard. That morning, I received hugs from everyone. That part I expected—or hoped for.
What I didn’t expect was what happened by the end of the day. We had planned a professional development day focused on our strategic plan, led by a skilled facilitator. She read the room and pivoted. In that pivot, something that had been held for a long time finally released. People cried. They named frustration, distrust, and hurt. They had been carrying it quietly—through my absence, through the uncertainty, through their own acts of covering and holding—and they needed somewhere to put it.
What landed hardest wasn’t any single thing that was said. It was a fracture I could see running through the teaching community—the evidence of how long people had been holding on without a place to put it down. My team and I followed up carefully: surveying faculty, working through the data, identifying what needed attention and repair.
I was still in my own recovery through all of it. I had to hold their pain while protecting my own healing—two things that don’t share a clean protocol. My body was still figuring things out; I ended up out of school again for three weeks in April. As someone who leads with compassion, the hardest discipline that spring was giving myself permission to keep recovering while the community needed me present. Headship had always asked me to give. That season asked me to receive and give at the same time, without apology.
By spring, I understood something I hadn’t before: You can do everything right and still not be able to rush what needs time. The community needed time. My body needed time. I had made staffing shifts, supporting talented teacher-leaders into new roles. But how those roles would work together—what connective tissue would hold them—was still unresolved.
Year 4 ended there, with more questions than answers.
Year 5: What the River Showed Me
Seven-and-a-half months post stem-cell transplant, I joined 20 heads of school on a weeklong river rafting trip. I had held it as a goalpost during treatment—something to aim my recovery toward, a proof of life I could keep in view. The focus of the trip was rediscovering purpose. We worked in small groups and pairs, doing quiet, reflective work about why we do what we do. The rest of the time, we were on the water—cut off from technology, surrounded by river and sky and the company of people who understood, without explanation, what the past few years had asked of each of us.
I wasn’t there to lead. I was there to listen. To build connection. To remember what belonging feels like when you’re not managing it—when you’re simply inside it.
That’s when my idea for St. Paul’s Center for Transformative Education came to me. Not from a whiteboard or a planning retreat or a consultant’s framework, but from the river. From the experience of people working in genuine community toward shared purpose, each one bringing their whole self, each one necessary. I came home knowing what I wanted to build: a structure that would let the talented teacher-leaders move into administrative roles to work together with coherence and shared direction. It was the connective tissue I had been searching for.
I never felt like I had been carrying things alone. This is something essential about my school—one is never left alone here. The Center wasn’t about redistributing a burden. It was about building the right architecture for the next chapter—director of student life, director of equity and belonging, dean of community engaged learning, dean of community wellness—so that I could begin turning outward. Toward stewardship. Toward fundraising. Toward telling our story beyond our walls.
The people who stepped into those roles were teachers—deeply experienced, long rooted in this school, integral to the fabric of who we are. They were ready. And that, it turns out, is one of the quiet measures of a healthy school: When the people who know it best are the ones who want to lead it forward.
Year 6: Steadiness, and What I’ve Stopped Trying to Prove
I am in my sixth year, midcareer. That phrase still feels strange and right at once.
What it feels like from the inside is steadiness. Not the absence of challenge—we still have seasons of grumbling, morale dips, the friction that comes with change. But underneath it, something has settled. I am not an impostor. I have cultivated trust over time, and I can feel it. I am more at ease with myself and with this role than I have ever been.
I’ve stopped trying to prove that I need to be anyone other than myself. After everything I’ve endured—the grief, the diagnosis, the treatment, the return, the reckoning—I don’t have time or energy for work that doesn’t feed my soul. I feel profoundly lucky to love what I do and do it as authentically myself. That’s not a small thing. It’s actually the whole thing. It’s also why ensuring that everyone in this community feels that same sense of belonging matters so deeply to me—because I know what it costs when you can’t be yourself, and I know what it opens up when you can.
Part of what makes that steadiness possible is knowing what the foundation looks like. The co-chairs who hired me saw me as part of their legacy—and they still do. They remain thought partners, animated by the mission and values of this school, invested in what it becomes. My current board chair has been an unwavering presence: a true partner who holds the board to high standards and has never wavered in her belief in me or in the work. A head of school is only as strong as the governance that holds her. I have been held well.
Over six years, my role has evolved from navigating one crisis after another to articulating a vision that honors the essence of this school while preparing students for an increasingly complex and polarized world. Headship, I’ve come to believe, is less about holding authority and more about holding purpose—steadying a community long enough for it to remember who it is and what it stands for. Strategy, crises, and initiatives come and go. What lasts is the culture a leader tends: how people care for one another, how truth is spoken, whether a school remembers its purpose even in the hardest moments.
This year, I can finally look outward. And when I do, I know exactly what I want to say.
St. Paul’s teaches what matters. We prepare students to meet the real world with confidence, compassion, and agency. Learning here is more than mastering content or solving for the right answer. It is learning how to listen and speak with care, how to collaborate and lead, how to apply knowledge to real problems that matter. It is about building meaningful relationships—knowing when to step up, when to step back, and how to show up for others. We value creativity, imagination, and nimble thinking. We expect students to engage when things are hard, unfamiliar, or uncomfortable—not to retreat, deflect, or decide it’s not their problem. This is how learners become capable, connected, and ready to shape the world they inherit.
I wrote those words months ago. They are not a mission statement drafted by committee—they are what six years of leading this school has clarified in me. That’s what midcareer feels like: not having more answers but having the right questions finally come into focus.
I am the fifth head of school at St. Paul’s. We are 50 years old, and the founding mission is still true. I stand on the shoulders of the people who stewarded this program before me, and I feel that weight—not as burden but as responsibility and gratitude.
If I had to name this role in a few words, I would say: keeper of the flame. Not the person who started the fire. Not the one who tends every corner of it every day. But the one who knows why it matters that it keeps burning—and who will not let it go out.
I’m still learning what that means. But I am no longer afraid that I don’t belong here. That, too, is something.