New heads arrive full of intention and ready to jump in. Then the job begins, and the theoretical meets reality. It’s a test of instincts and endurance, asking leaders to listen deeply while still moving forward.
This article appeared as "The Power of Alignment” in the Summer 2026 issue of Independent School.
After watching our girls’ lacrosse team beat a rival, I walked to Ocean Beach to catch the sunset—one of the many perks of living in San Francisco. Just before dusk, a family of three passed by, a mom and dad sandwiching a kiddo no older than 4. He kept asking to climb onto a retaining wall, drawn by the promise of a new vantage point and the thrill of a small, manageable risk. Eventually, Dad dutifully plopped him on the 4-foot wall. The kid froze, looked around, steadied himself, and took the smallest of steps forward. With each moment, his steps grew longer and more confident. Soon, he was racing along the wall, his parents jogging to keep up.
That kid is me—drawn forward by curiosity and caution in equal measure. I have the great privilege of leading Urban School of San Francisco (CA) as a first-time, first-year head of school. There’s a certain naiveté in writing about headship while still new enough to fear jinxing what has, so far, been a good first year. I don’t have all the answers or the lived wisdom of a seasoned head, but I know why I chose this role. Like my young wall-walking friend, I was drawn by the challenge and the possibility of something more.
In reflecting on my first year, I offer my insights as an act of service and an expression of love for the role of headship. Even when the work is challenging—the tensions, the surprises—it remains deeply compelling, and the learning feels inseparable from the job itself. In the spirit of learning, this is my best attempt to unpack my experiences, with reflection, humility, and vulnerability.
Being in the right place. Urban, simply, is a good match for me. I wish I could have gone here as a kid. It’s a quirky, nerdy, pro-social community of learners who are interesting and curious, attentive to the world beyond, and energized by the vitality of the mind. It’s a place that speaks openly about joy and about the power of adolescence. The faculty and staff, the parents, and the board are talented, supportive, and deeply committed to breathing life into the mission. Most important, the students remind me every day why I chose education in the first place—I’m confident they will be thoughtful stewards and leaders of our world, whatever challenges lie ahead.
I’m not bringing my full self—and that’s OK. It is often said that you should bring your whole self to work—and I once advocated for that, too. Stepping into headship, I’ve pivoted. I show up to Urban as a more curated, though still authentic, version of myself, not quite confident (or foolhardy) enough to bring my full self. Urban affirms my intersectional queer, multiracial, nerdy identity. I wouldn’t have come if it didn’t. Still, I’m a big feeler, tenderhearted by nature, and I know I must hold some of that in check most days as a head. I balk at advice to never take things personally; I do take this work personally because I care so much for this school and its people. Rather than treating those traits as kryptonite, I’m learning to see them as a superpower—one that requires restraint. My responsibility is to continually scan and sense how much of myself to share with the community: measured vulnerability, if such a thing exists.
Imposter syndrome remains real. How fast am I moving along my metaphorical retaining wall a year into headship? Some days, I feel myself taking confident steps forward, advancing conversations, decisions, and processes alongside my colleagues; other days, I’m frozen in place, steadying myself as I wrestle with the inevitable right-versus-right decisions that define headship. Rarely, if ever, do I sprint, and I’m OK with that. Nearly every day, I pause and think, I’m the head of school. How is that even possible? I’m learning to channel that feeling into motivation: to keep learning, showing up, and doing the next right thing.
Headship doesn’t have to be lonely. What do I do when I’m feeling imposter syndrome creep in? Call a fellow educator. Given that one of the roots of imposter syndrome is an anxiety about worth and performance, I’ve found that connection paired with curiosity can be a powerful salve. Sometimes it’s a quick conversation with another head or a short text exchange with a mentor or my leadership coach. And despite the advice to be guarded with colleagues, a conversation with a member of the leadership team about a question I’m holding can also be exactly what I need. My team has done a masterful job of supporting my transition into the community, and turning outward has proven more valuable than I expected. While some responsibilities rest with me and me alone as head, whenever I can, I choose connection and collaboration.
Love the learning in the work. Schools are about learning. They’re spaces for idea creation, challenge, and the kind of friction essential for growth, for students and adults alike. I am loving the chance to learn alongside Urban: its history and the city of San Francisco, as well as the intricacies of leading a complex enterprise. Risk, finances, and development aren’t all in my natural wheelhouse, but I’m learning as quickly and thoughtfully as I can to best steward the school’s mission. I’m also learning to embrace my role as head more fully as conductor, knowing I can’t—and shouldn’t—track every detail of every decision. That’s where that trust and collaboration matter most.
Prioritizing time in the community matters. Simply put, that’s where the stories are. If we are to lead our community in sensemaking (an underrated but essential skill for headship), we must be in it, not apart from it. I know this runs counter to some views of headship, but I have students in and out of the office periodically throughout the day. When I substitute for a class, hop on the team bus for a volleyball playoff game, opt to advise a group of seniors for the year, invite a faculty member in for a casual drop-by, or pick up the saxophone to play in the chamber ensemble, it signals that I, above all else, am still a learner and a human with interests who embraces joy. It says that I want to connect, that I delight in what we share as a community. It also signals a collective spirit; the individualistic streak that can surface in our schools is palpable—and frankly frustrating. We do this work as curators and sustainers of community. Being in the action of it all matters.
The practice of self-management. There’s a certain irony in leadership; it’s often associated with getting things done the leader’s way—an outdated trope, perhaps, or the residue of a heroic narrative. (Trust me, I’m a first-born Capricorn; I understand wanting things my way.) Yet almost a year into headship, I’ve learned that one of the best ways I can serve Urban is by managing myself. Headship carries an extraordinary cognitive and psychological load, shaped by the tension between what I sense the school needs and what the community believes it needs. Add questions of timing, readiness for change, the humanity of each person in our community, and the sheer magnitude of the world beyond our campus, and the temptation to fix, move, and cast a bold vision can feel nearly irresistible in a first year. Still, my work as chief architect for change depends on something quieter: deep listening. Restraint. Careful planning. Measuring twice before cutting once. This work isn’t about my “agenda”—it’s about articulating our collective vision.
A Millennial Mindset
In The Power of Bridging: How to Build a World Where We All Belong, John A. Powell suggests that our sense of well-being depends on the stability of our environments. Amid the rapid and expansive changes shaping society, including the role of schools and education, he warns that when change “happens too fast, we are not only stressed but likely to be overwhelmed,” even to the point of becoming strangers to ourselves. I can’t help but think about how this applies to the ontology of headship: head as sensemaker, conductor, architect, weathermaker. It’s a lot to ask of anyone, yet it underscores the importance of self-management and reflective practice. At its core, the question is this: How can I be a steadying presence for the community I am entrusted to care for and ultimately evolve?
All of this leads me to a closing question, one that continues to stoke my curiosity and could shape headship in the years ahead. For a long time, we’ve focused on the changing demographics of the families, students, faculty, and staff in our schools. But what about the changing demographics of the head? I’m a proud millennial and embrace many of the traits associated with my generation—continuous learning, comfort with technology, purpose-driven work, and a strong drive to grow. This is not to suggest that the heads I’ve learned from aren’t these things; they absolutely are. Still, many of these traits are, in some ways, embedded in the millennial DNA.
I often talk with Tom Taylor—a friend, fellow millennial, and head at The Paideia School (GA)— about what it means to be millennials leading schools. Not to dismiss wisdom of the past but to bring a complementary perspective to the role. We both suspect that there’s something worth examining here, particularly in millennials’ strong orientation toward the concept of team. How might this shape future headships? Could it deepen alignment with boards around strategic vision and futures thinking? Might it underscore the importance of investing in collective capacity—building teams aligned around shared principles and priorities? And could it demand a new skill set for headship, one centered on coaching and developing those around us? I hope so—and I hope, as a field, we continue to make room for this version of headship, one sustained by curiosity and rooted in a collectivist spirit.
I hope I never shake the desire for the challenge, the new vantage point, and growth—like the little boy on the wall—even on the hardest days of headship. The work requires a steadiness, a restraint, and a big-hearted sense of care. And, even when uncertainty strikes, as it inevitably will, the work also asks us to keep moving forward. One step at a time. Curious about what comes next.