Why I Am a Head of School

                During a recent conversation with a trustee, he remarked, “I don’t know how or why you do what you do, but I’m glad you do.” That same afternoon my board president asked, apropos of nothing, “Do you feel we pay you enough?”  Such comments are not that uncommon. They call to mind a conversation I had with another head of school.  As usually happens, we discussed the challenges of the role and shared some war stories. Towards the end he said, “The things we do, we have to be crazy.” In such conversations people often make such off-hand comments, sort of a hybrid between self-deprecation and venting. But it draws attention to the rather ludicrous way some of us choose to put ourselves in stressful leadership positions, whether in independent schools or any field. I believe we are called rather than crazy.

                But why? It’s a very complex and demanding job. (See this recent article “A Complex Web: The New Normal for Superintendents.” Different role in different world, but similar issues.) That’s not whining. In fact, it’s quite the opposite. I thrive on the myriad aspects of the role, of the unpredictability, of all the moving pieces. There’s also something ethereal about it. I believe school heads need to reflect quite regularly, and this is an essential question. However our personal stories may vary, the answers can sustain and ground us. For me, they are framed by what I call my “P Statement,” which I wrote in my letter to self at the Institute for New Heads. The abbreviated version reads, “You are at this place at a point in time for a particular purpose because of the person you are.”[i] In unpacking this a bit on a personal level, I hope something resonates and affirms your work, whatever it may be.

Sometimes I wonder how I ended up leading an independent school. I attended Catholic elementary school and then went to public schools. Throughout college I had no clear career goals, majoring in English because that meant loads of reading and writing and thinking about big ideas. Education never entered my mind…until an insightful career counselor studied my personality, interests, soccer background, coaching experience, and work with kids; and told me to consider working at an independent school.  Clueless what that meant, I felt drawn to the idea. I thought I would try it for a little while. Thirty years later, here I am.

Therein lies the real irony. Growing up, I couldn't wait to be done with school. I loved learning, but I hated school. My parents knew what was coming at all conferences and on all progress reports: some version of very-bright-but-does-not work-to-his-potential. Simply put, I was bored. I found the work rote and uninspiring, the teachers too rigid in approach and expectations. Two examples capture my frustration. In middle school I could not move ahead in math because I lost one point due to a computational error on a test despite my strong conceptual grasp. Throughout school I asked to be given alternative books to read because I already had read the assigned text, only to be told no. Occasional teachers engaged me through wonderful projects and challenging discussions or assignments, but most of the time I could race through the checklist. Only towards the end of college—during seminars, independent studies, and a thesis—did I dive into academic study.

To deepen the irony, my experience led me to education. There had to be, I believed, better ways for schools to work. Now I know there are. As the leader of an independent school, I have the incredible opportunity to leverage our freedom we to create amazing places that reveal the infinite possibilities of a meaningful education. One not determined by curricular standards, data, benchmarks, college placement, or exit exams. Instead, one about less quantifiable ideals—the soul of the matter . The connections in a caring community where diverse people are valued for what they can offer. The courage to take risks in search of understanding. The awareness of one’s potential and growing towards fulfilling it. The development of a supple mind, a healthy body, and a kind heart.  A rich atmosphere that prompts people to explore widely and to plumb the depths of themselves. The realization of a purpose beyond oneself.

I find thinking of my work this was to be both inspirational and aspirational. As head, I have the sacred responsibility of holding forth this vision towards which we keep striving. The hope is that others will see the work the same way.  Then steady, determined progress becomes the default setting. And the less savory parts of the job become more digestible.

More than anything, the work truly matters. Of course, we’re often left to wonder if we have succeeded. Then, out of the blue, we hear from an alum who is doing wonderfully. That person has become contributing positively to the world. He or she then explains how your school helped that happen. For an educator, what’s better?

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[i] If you’re interested, the entire letter reads:

Dear Self,

Today, high or low, and every day, great or crummy, remember the P’s.

Point—You are at a particular point. It’s less than a millennial blink.

Place—You are at a particular place, a place you love and are meant to be right now.

Person—You are a particular person, with your unique mix of human qualities, both saintly and devilish.

Purpose—You have a particular purpose, to this place and to your person, and they are intersecting at this point in time. Serve both well.