“Aren’t you glad you got out of school headship when you did?” I have heard this question, or variations on this theme, often over the last year, and I have generally answered in the affirmative. What was already a difficult occupation has become monumentally more pressured since the onset of Covid. And the challenges presented by the pandemic have been exacerbated by the long overdue and often painful reckoning many schools have encountered in the wake of George Floyd’s death. Layered over all of this has been an excruciating election season when many heads have had to navigate heightened and sensitive political passions in their communities. Yet there is some very good news here for independent schools; despite the apparent hurdles, I encounter remarkable people on a daily basis eagerly seeking to lead schools into the future.

In June of 2017, I retired from school headship. The reasons were uncomplicated; after 22 years in the role, I was ready to try something different. There were certainly elements of the job from which I was delighted to walk away. Decades of discussions about dress codes of various regional, philosophical and cultural sorts, among other mundane persistent topics, no longer held any interest for me. I had had my fill of emotionally-overwrought parents, teachers, trustees, students and school neighbors. I had navigated through a multitude of crises over the years, large and small, from unexpected social eruptions to the tragic passing of members of my immediate school community; all of these situations take a cumulative toll on the psyche and energy reserves of a school head. It was a sometimes lonely and stressful occupation. In spite of all that, however, I continue to regard headship as the best job in the world and the most wonderful experience of my life.

It does not surprise me that even in this most trying of school years I have had many rich conversations with people who aspire to headship. The primary motive for most of these people is the desire to serve, inspire and build communities. The problems of the last year, rather than dampening this urge, have instead stimulated it. It strikes many educators that in their lifetimes there has been no more propitious and essential moment to take a stand for character, reason, compassion, equality, and service to others.

The last several months have induced an unprecedented platform for change and innovation in education. While everyone longs to return to some sort of remembered “normal,” the fact is that we will never fully go back. Teachers and administrators have adapted with remarkable skill and flexibility, and they have found some of those changes to be things that they want to retain in their practice and approach. This includes technological adaptations, but it also incorporates adjustments to curriculum, pedagogy, the function and organization of schools, and fundamental ways that we approach education at every level. Has there ever been a moment in recent history more primed to witness remarkable progress and positive change in education?

It is probable that the next 10 years in schools will look profoundly different than the last 10. Heads have the opportunity, the responsibility, the imperative to rethink schools, and to build dedicated teams of people to collaborate in this work. This must include anti-racism work, the role and ongoing utilization of remote learning, the economic model of independent schools, and what it means to be "educated" beyond 2021, among many other topics.

I asked several of my colleagues at RG175 what they thought about the question of why one would want to be a head in the years ahead and they came to the same or similar conclusions to mine. One of my partners, Tom Hudnut, offered some particularly poignant observations that I want to share. He said, “Having lived, and led, through the crises of 2020 that you cite, people should know that this perfect storm, this weird confluence of negative occurrences, is unlikely to happen again. We school teachers are born optimists, so believing that shouldn’t be too difficult.”

He added, “Second, regardless of the circumstances in which we find ourselves, children need to be taught, sensitive and able teachers need to be hired, money needs to be raised, schools need to be led. Why not you, Prospective Head? The need has never been greater for school leaders with wisdom and a deft touch in dealing with people.”

“Third, most schoolchildren in America, regardless of the kind of school they attend, have lost a great deal during the pandemic in terms of social-emotional growth and academic attainment. Someone who has the ability to galvanize a school community, rally people to the school’s cause, and motivate the group’s progress will always be in demand.”

He finished by saying, “Being a Head of School is still a great job. The opportunity to mold and improve a community, inspire students and teachers and families, and create a positive ethos that permeates people’s lives–what other job affords that?”

I am cheered by these thoughts even as we pass through dark moments. I deeply hope those who might aspire to headship will continue to be motivated in these times to embrace what can be the greatest job in the world.