This article is part of our yearlong Headship series, which explores a different aspect of headship each month on the Independent Ideas blog.
Star Trek’s Starfleet Headquarters is in San Francisco. And it certainly felt that way the last time the five of us, all heads of school in California, were there. We had gathered for a final planning session ahead of our CAIS Heads–Trustees Conference presentation on head of school burnout.
We were there as professionals. However, our relationship began years earlier during our service on the CAIS board, where governance meetings slowly gave way to friendship. In the lull between logistics and learning objectives, in that small human space where exhaustion gives way to candor, we discovered something else entirely: We were all Trekkies.
What began as an aside quickly became a taxonomy. By the time we left the room, we had nicknames. By that evening, the conversation had shifted to a text thread. By the next morning, we weren’t just five heads of school preparing a session on burnout—we were a fleet.
Our session was co-led by Amada Torres, the NAIS guru of data and dashboards—the person who reminds us, gently but persistently, that intuition is a hypothesis until proven by evidence. She was our Spock, our collective science officer.
It was there—in the banter, in the bridge chatter of text messages—that we began to reflect on our own journeys. Our schools, we realized, were not unlike starships: each navigating hostile environments, shifting political terrain, unpredictable anomalies of culture and climate. Each requiring a captain.
More than nicknames—these were metaphoric monikers, capturing the peculiar contradictions of headship: the expectation that we be explorers and engineers, diplomats and disciplinarians, visionaries and mechanics, all while navigating a universe that seems to be expanding faster than our ability to chart it. There are moments when the captain's chair feels less like a seat of command and more like a place from which to contemplate just how lost in space one can become. And yet, each of us had found our way to the bridge by a different route, discovering that there is no single Starfleet Academy, no prescribed path to command, and certainly no manual for the anomalies we encounter along the way.
As Dr. Soran reminds us in Star Trek: Generations, “time is the fire in which we burn.”
But as the original poem insists, “time is also the school in which we learn.”
Each of the five heads in our fleet had taken a different route to the captain’s chair. Here are their stories—and the Star Trek captains whose journeys best reflected their own.
Captain #1: Benjamin Sisko
Ole Jorgenson, head of school at Almaden Country Day School (CA), was our Benjamin Sisko. He began in international schools, returned home to care for ailing parents, taught in public schools, then returned overseas again. He met his partner abroad and came back to the United States to begin an administrative career in public education, hoping to serve as a superintendent in a Title I district.
But when it seemed like the No Child Left Behind Act had rendered children—and the communities that nurtured them—as data points to be labeled as failures, he opted out. On what he calls a lark, he applied to be the head of a private boarding school in Hawai‘i, despite having no experience in independent or boarding schools.
He got the job, only to discover months later that the first search had failed, seasoned heads had withdrawn upon meeting the board, and he had unknowingly walked into dysfunction.
Four board chairs in five years.
A culture to rebuild.
A team to hire—and fire.
Like Sisko arriving at a broken Deep Space Nine, Jorgenson inherited not a ship, but a station barely holding orbit. His leadership team—Japanese Hawaiian women who anchored the institution through change—became his bridge crew. When he departed, much of what they had built unraveled.
Now, he leads an under-resourced, unpretentious school aligned with his values.
Sisko would understand.
Captain #2: Kathryn Janeway
Dr. Cindy Chun, head of school at Peninsula Heritage School (CA), brought Kathryn Janeway to mind. She never wanted to be a head. She began as a preschool teacher, moved into kindergarten, and over 14 years taught nearly every grade in the lower school. Even as she pursued her doctorate, she resisted administrative roles. She loved the classroom—the lightbulb moments, the proximity to learning.
However, her advisor suggested her impact might be exponential outside the classroom. Her eventual move into an assistant headship revealed a gift for systems leadership—curriculum, technology, communications, even finance. She absorbed responsibility quietly, effectively running the school behind the scenes.
And then came the signs.
A broken wrist.
An emergency appendectomy.
A lump.
Her body, like Voyager’s hull under strain, registering impact before her mind acknowledged it.
She left a toxic environment and struggled through a season of unexplained rejections—until mentors intervened. She served one year as assistant head, allowing the community to get to know her before stepping into headship.
Eight years later, she remains.
Janeway would call that endurance.
Captain #3: Jean-Luc Picard
Phil Gutierrez, director of the California Association of Independent Schools, fit the Jean-Luc Picard role. His journey is perhaps the most traditional.
He began as a high school English teacher. Chaired a self-study. Served as dean.
Moved into admissions. Then assistant head for advancement and external affairs.
After completing the NAIS Aspiring Heads program, he spent several years interviewing before securing his first headship.
Like Picard, Gutierrez prepared. He studied. He waited for the right command.
He wanted to remain in the Bay Area and at the secondary level, limiting his search with intention. Picard’s enterprise was not assigned by accident; it was earned through readiness. And just as Picard once led the federation against the Borg—in our minds a manifestation of all things dystopian with AI—Gutierrez now brings that same prepared steadiness to his role as the director of the CAIS.
We felt Captain Philcard was an appropriate nickname.
Captain #4: Christopher Pike
Brad Weaver, head of school at Sonoma Country Day School, emerged as our Christopher Pike. He was tapped by a mentor into public school leadership before directing a small American international school overseas.
He valued working with a board in an independent setting that was less constrained by bureaucracy. Returning stateside, he took a division head role to learn the nuances of independent school leadership before pursuing headship again after earning his doctorate.
He skipped traditional preparatory programs, later noting he had missed networking opportunities—but also that this very group had helped fill that gap.
Pike, too, was called before he was fully prepared—leading through literal fires to position his community for success.
He grew into command.
Captain #5: James T. Kirk
As for me, Kalyan Balaven, my peers cast me as James T. Kirk. I came from The Athenian School (CA), a school that has produced an improbable number of heads of school. Almost as if it were Starfleet Academy.
But my own journey was nontraditional: lawyer first, educator second, then climbing the ranks of independent school leadership.
Kirk was never meant to follow the manual; he followed his heart. As did I.
Like Kirk, when I sat in the Captain’s Chair at Dunn School (CA), where I currently am head, I did not believe in the no-win scenario of an under-resourced school in these times of enrollment decline and the five great disruptions—post-pandemic, smartphone addiction, narrowcasting/cancel culture, the disruption of social media, and AI—we are all navigating. And as my peers pointed out, I’m ready to beam down to the planet—albeit not wearing a red shirt—whether for admission or advancement while also leading from the bridge.
They also felt I was the one most likely to tamper with the computer to save everyone in a Kobayashi Maru simulation.
Leading Our Fleet
Our thread became a constellation of ships—each navigating time’s fire, each learning in time’s school.
Sometime after the CAIS session, we realized that burnout, like warp drive, is not merely about speed. It’s about endurance. About systems that support captains. About crews who trust them. About institutions willing to learn as they burn.
Because in the end, our schools are vessels traveling through uncertain terrain toward futures we cannot yet see. And for a time, we are entrusted with the helm.