This article appeared as "On Leave” in the Summer 2022 issue of Independent School.When I first started as head of school at Westover School (CT) in 2015, a head from a neighboring school very kindly helped me acclimate to my new community by introducing me to some important people, including a female executive director at a local hospital. By the time we met to have coffee and connect, she had accepted another position out of state and was about to move away. She’d overseen a merger—it was necessary, but it had stressed the internal culture—and it had taken a lot out of her. She decided it was time to move on to the next challenge, admitting that she was an adrenaline junkie but acknowledging that there was a price to be paid. At the time, I thought to myself, Hospitals are such stressful environments. Glad I’m not an adrenaline junkie.
However, as I started my new role, I began to wonder whether I was an adrenaline junkie, too. The first few months of headship were confusing and overwhelming. Many of the school’s core, complex problems were starting to surface, yet I believed in the school’s vision and powered ahead. I tangled with some bullying behavior right out of the gate, and I was taken aback by the audacity and entitlement embedded in some aspects of the culture that had nothing to do with serving the students. This just strengthened my resolve to press on. This, I was starting to realize, was a kind of adrenaline cycle.
In the Beginning
When I think about how I got here, I reflect on what fueled me in my work—intensity, risk-taking, frequently being personally challenged to solve difficult problems, a passion to improve mission delivery. I started as a teacher, then a department head. I learned a lot from seeing other people struggle to form and execute a vision. Execution often seemed to be the most fraught. I grew to fully appreciate just how important strong, clear leadership is to assess what will move a school forward in serving students. I realized that my skills, which combined psychology, empathy, and strategy, made me a strong candidate for and led me to administration.As a senior administrator, I oversaw and led durable, impactful change. It was hard, but it didn’t feel impossible. I did this for 16 years at one school, first making specific curricular changes as a department head, leading larger-scale programmatic change as academic dean, and then finally schoolwide change as an assistant head. The challenges were complex, varied, and interesting, with some key allies and persistent resisters. It indeed was an adrenaline junkie cycle—challenges, triumphs, setbacks, repeat.
As a head of school, the challenges became more complex and also fundamental—for one, basic economic survival; relevance in a quickly changing marketplace a close second. And that’s where I’d say the electric charge I got from rising to the challenge and surmounting obstacles became addictive and led me to get caught up in this cycle. No matter how low the lows—and there were some pretty bleak periods—there was a choice or a decision that changed the dynamic. We’d see the enrollment numbers rise, the fundraising dollars increase, and a beautiful new student commons change student social life, for example, or the college list feature a wider range of and more selective schools. One of the greatest moments was when a four-year student of color gave a keynote speech on Revisit Day 2021 about how the school is all about love. The rush from that progress was profound.
But leading all of this work has taken a toll. So, this past fall I gave my school notice that I would step down as head at the end of the 2021–2022 school year. It was perhaps the hardest professional decision of my career, but I am sure that it’s the right one for me.
Back to Reality
When I first took the position as head of school, an old friend who was already a head sent me a congratulatory note that ended cheekily with “When you need someone to talk to about all the things they didn’t tell you about, I’m here.” I laughed at the time, but I thought about this so much during the first few years.The pandemic has dramatically brought to the forefront the underlying problems with our aging, creaky independent school model. While intellectually we may understand we are running highly complex nonprofit businesses with ever-increasing demands in terms of governance, resources, fundraising, constituency relations, accessibility and affordability, human resource management, and legal liabilities at every turn, the reality of these demands in practice is a recipe for burnout.
We are facing a general collapse in 20th century American structures of society. There are basic questions about the durability of American democracy and a lack of trust in the world that engenders cries for “transparency” here, there, and everywhere—even though context and nuance may be lost in the process. Judgments are both glib and absolute, perpetuated easily through digital media. It is an era of being publicly shamed. You can never predict which decision you make might prompt a social media campaign that could damage your school’s reputation or your own. As leaders, we know it’s impossible to make everyone happy, but now there is potentially a steep and time-consuming consequence.
And while independent schools are not immune to these impacts and must face hard questions about our purpose and future, too often we have responded reflexively to current market demands, trying to be everything to everyone.
Exit Signs
People yearn for parental figures. And these types of parental figures, which we believe have existed in the past in all sorts of institutions (government, businesses, and heads in our schools), might not have even really existed at all. They’re illusions, lore. But they’ve become part of our story whether they were real or not. And even if we know that these people might not have been real, we draw comfort from believing they existed—and we still want that.The effort to uphold this role—particularly during a pandemic—can last only so long. During the height of COVID-19, I perceived that faculty and staff members wanted more from me—more personal attention, more of a sense of individualized commitment and care, more clear answers, more reassurance. To keep my own sanity in a world turned upside down, I had to construct and then live within boundaries that made it possible for me to do my job. I could see the disappointment this created, the unmet longing I walked away from. I felt deeply conflicted.
I had seen many heads unable to let go, and I had judged them for not being able to see that it was time to step away. And sure, there are financial considerations and stability considerations when it comes to leaving a job. When I started to seriously think about stepping down, my underlying fear was, what will happen when I let all this go? Will my Jenga tower fall apart? And really, more relevantly, what does this say about me, both that I’m reluctant to let it go and that I’m worried about how fragile this edifice really is?
As heads, we become so personally identified with our schools, it’s difficult to discern where we stop and where the school begins. And that’s part of this essential problem of the sustainability of the job. A leader makes a difference, but the totality of the school can’t be epitomized in the person. That is ultimately bad for the school and impossible for a head to carry that weight.
Making the Call
The enforced solitude of the pandemic prompted me to make some essential recalculations of what I want my life to be. Often, I felt as if I had become a one-dimensional human: a head of school. And in the end, that’s my professional position, not my identity. During this period of headship, I have let so many important friendships fall by the wayside. I haven’t been the aunt or sister I want to be. And most important to me, I can’t be the daughter I want to be to my elderly parents in their final years when it’s time for me to return all the love and care they gave me that made me the person I am today.There were some personal reasons that influenced my decision, but I’ve thought about what could have prevented me from being in this position of wanting to let go. Of course, it is hard to run a school, and no head is an expert in all the areas it takes to make a school thrive. Examining the head-board relationship also led me to my decision. Boards have a lot on their plate, and they are volunteers who are long on passion and short on time. Heads are prioritizing the work that needs collaboration with the board (approving budgets, fundraising, keeping them up to date, approving COVID-19 policies, etc.). Long-term, generative thinking about our changing context has been in short supply. This reality leads me to wonder how boards can hire a head for a focused purpose rather than expecting one person to be everything to everyone.
Ideally, at the time of hiring, there should also be at least a subset of the board who is open and supportive around conversations about contract length, what a head needs to stay relevant (continuing education, a sabbatical, executive coaching), or how to support a head to transition out if all agree it’s time for a fresh set of eyes. Thinking in these ways should not feel disloyal or like a lack of confidence in leadership. Instead, it’s an acknowledgment that we are all committed to a growth mindset and that the days of a 20-year head are probably over.
I could have chosen to keep going. But it was time to address my adrenaline addiction. It was extremely hard to share the news of my departure with my senior team, a group of outrageously talented professionals and wonderful people, a group I had built so carefully and tried to support in order to drive the school’s mission forward. But it wouldn’t have been any easier a year or two or even five years from now.
As I walk into a quieter summer, my first priority is to renounce the adrenaline merry-go-round and get back in touch with the original engine that drove me to want to connect with and serve kids. I look forward to having the time to unpack the many issues of headship and expectations around the role. Fundamental change in education has always been on the horizon, and now it is here. There’s such opportunity for schools, heads, faculty and staff members, students, and families. In the next stage of my independent school career, I vow to be part of positive change, to keep living the mission-driven dream, and to be even more determined to keep trying to make the dream a reality.