Sustainability and the Headship – A Prizmah Conference Reflection

I spent the first part of this week at the Prizmah conference, a gathering of over 1000 Jewish day school professionals that happens every two years. It was motivating and energizing to be with so many liked-minded idealistic fellow Jewish educators, who are so deeply engaged in this holy work. 

The conversation I had most frequently at the Prizmah conference was about sustainability (or rather, the lack of sustainability) in the headship of Jewish day schools. I remember clearly during my first few years asking colleagues: How can I do this job for 20 years? It’s not possible! The most common response was about how expectations had changed, that they were now more and more unreasonable, and that may be true (I have no personal comparison). But I think there are some deeper issues at play that are worth thinking through, that took me a long time to gain clarity about – and I’m still hardly out of the woods on this question. 

One important framing: what I write below is about the psychological aspect of the headship, and the challenge it presents irrespective of circumstances. There are, of course, many contextual circumstances that can make the job harder or easier: unrealistic expectations from parents; bad behavior by parents; unhelpful or challenging lay leaders; the challenges to family life. All of these can be true, and are unfortunately common.  And while I think these should be part of a larger conversation about sustainability, I’m going to limit myself to the psychological sphere, one I hear less about, and think deserves more attention and elucidation. 

It’s worth starting at the beginning: there is a dramatic psychological difference between school leadership in general, and the headship. Leading others in general comes with increased responsibility, the need to learn to say no and accept people’s frustration and disappointment, amongst other inter- and intra-personal skills. But being the CEO, the person who’s ultimately in charge, who is finally responsible, is an entirely different mindset, and it weighs much much more heavily on the mind. This is not a difference in degree but kind, and it’s hard to explain this to someone who has not occupied this particular leadership seat.  Knowing that the greatest part of what the institution becomes lies in your lap; that the problems of the greatest complexity end up on your plate; the volume of decisions – these realities sit differently, more heavily, than non-CEO leadership.  

This is compounded by a conflating factor in Jewish day schools, and possibly in education altogether, which is its inherent idealism. We do the work because it’s God’s work, because we want to help birth the better world that education is tasked with, because we are in it for the mission of our institutions. And when you do something with a mission in mind, boundaries are much harder to identify and draw.  When is it enough for a child? When is it enough when you know that putting need X lower on the list of priorities means some child will not succeed and may ever suffer?  When do you put Torah second to your own needs?

One of the sessions I learned a ton from at the conference was given by the Harvard ‘happiness’ psychologist, Tal ben Shachar. He referenced a study Adam Grant shared in his book Give and Take.  Grant identified three types of people: givers (who give without the expectation of getting something in return), takers (put their personal interests first) and matchers (who operate on the grounds of reciprocity). What he found was that Givers were at the top of the professional food chain – good news! Their generosity bore fruit. In the middle – Matchers and Takers, and at the bottom – Givers again! How were Givers both overrepresented at the top and bottom of the success ladder? The difference Grant found: Givers who gave to themselves as well as others were at the top, while those who neglected themselves were at the bottom. 

Givers are much like our educational idealists – they need to focus on themselves, but often do not, and when they do not, they burn out. More on what it  might look like to give to one’s self in a moment.  

A third factor, which challenges some of us, though not others, is the degree to which we are introverts or extroverts. For the former, the headship presents unique challenges. In the headship, more than any other leadership position, people carefully read your every move, emotion, and interaction.  Being ‘off’ or not present is not a luxury we can afford. This is even more true in Orthodox schools where the Heads usually live in the community they work in. Even in the nicest communities (and I live in one!) where parents don’t talk to the Head on Shabbat about school related issues, there is no capacity to be ‘off’, or inattentive to one’s presentation and persona.  For introverts, this can be incredibly draining. 

So, in Grant’s terms, what does giving to yourself look like? At it simplest it’s advice you’ll not be surprised about, even if it’s easier to say than do: exercise at least three times a week; sleep more than you probably are; take time to meditate or at least takes regular breaks; turn off your phone or put it on a shelf, whether it’s email or social media that draws you in; make sure to prioritize time for your most important relationships; actually don’t check email when you put on your vacation responder (!).  And while all this is true and necessary, and I mean truly necessary, I think there’s another piece here that I’ve heard less discussed and which I think is tremendously important – the importance of creating boundaries, both psychological and social. 

I’m embarrassed when I think about (let alone share) this story, but I think it will serve my point well.  At one of my lowest points in COVID I was having a conversation with my coach and must have mentioned that I never closed my office door. She was astounded (incredulous?) and asked why. I said that I felt it was my responsibility as the leader to be present for anyone who needed me, so how could I close the door? Wouldn’t that send a message that I was unavailable to the people who worked for me? And isn’t that the wrong message?  I was the worst kind of Adam Grant Giver. That’s the voice of the idealist who has poor boundaries, who thinks the need to be responsible never ends. Perhaps it’s also the voice of someone who wants to be needed – but that would take us in another direction.

This began a long conversation about where my boundaries were. Not just the physical ones, like closing the door (which became part of a larger conversation about who has access to me and when, and who controls how my time is spent ( is it just because someone asked for it??)), but the psychological ones. I literally needed to give myself permission to create boundaries in my own mind. It’s not just about not checking email when I’m home or on vacation, but creating a new story in my mind. In that story school is not present, or its importance is discounted. In that story I say ‘no’ to being needed, to having responsibility when my wife or child are in front of me, or when I need to make sure I finish my learning seder that day rather than respond to yet another email.  I had to do this because I could never just say that I wouldn’t think about school. That’s like when you tell someone not to think about pink elephants, all they can think about are pink elephants. I needed a different story, a story that created a boundary in my mind between school and home, work and davening, between not just the daily pressures of work and that last negative parent interaction, but the underlying responsibilities that I talked about above.  

The principle of boundaries applies, as well, to the question of public presence, though this is a more sensitive topic which I’ll leave for another time. 

Is there a way to learn some of what I described above through anything but experience?  I think part of this does fall into that category of things that have to be lived to be understood, that words can’t quite address. That said, I think making these struggles public, and more heads thinking through this practice out loud, can only help our peers who are early in their careers and learning to adjust. I think lay leaders, board chairs in particular, need a deeper awareness of what their Heads are facing, and the toll it takes. I think boards need to have a more explicit conversation, amongst themselves, about what they need to do to ensure that their Heads are protected and sustainable. At the conference there were a couple of Heads who mentioned that they took anywhere from 2-5 month sabbaticals, and credited this to their longevity. Most of us could not imagine such a reality.

A final note.  There are lots of other reasons why a headship may or may not be sustainable, as I mentioned above.  My goal here is to address an area I haven’t seen discussed before, the psychological sphere in particular, and provide some thinking I hope can help others. It’s the beginning of a conversation.