“We Want You to Stay”: A Lesson in Letting Go

Sixteen years of telling parents to step back — and what it feels like to finally do it myself

This week, a group of first graders stopped me in the hallway.

“We want you to stay,” one of them said, “and the girl.”

For context, I’m weeks away from ending my sixteen-year tenure as head of Georgetown Day School. The “girl” is Tori Jueds, who will become GDS’s sixth head on July 1st. She is a warm, accomplished educator with decades of experience and, for the record, she is a woman, not a girl. But she is new, and I am leaving, and this is how first graders make sense of transitions: with open hearts and the words they have.

I told them that they are going to love her. What I was thinking was something else: I want to stay too. I’m going to miss watching you grow up. What a privilege it has been to be part of so many journeys like yours. I am mourning, a little, the chance to see yours all the way through.

There are two kinds of moments in these final weeks.

The first kind leaves me momentarily teary, even unsteady on my feet. The honesty of a first grader. An alum who drove hours to attend our reunion barbecue and says, “I came back to see you.” Sometimes I remember the alums vividly—who they were at seventeen, what they were working through, what we laughed about together. With others, I confess, I don’t remember them at all. It doesn’t matter. In either case, I feel the same gratitude: to know I’ve been part of their journey, even in ways I can no longer trace.

The second kind of moment makes me think I could leave tomorrow. The knotty personnel issue that seems to resist every solution. The parent who is furious about a discipline decision. The complex problem I’ve worked on for years and still haven’t solved. These moments don’t make me love GDS any less. They remind me instead that sixteen years is a long time, and that institutions sometimes benefit from a fresh set of eyes.

I’m trying to stay present to both kinds of moments. Transitions are complicated.

For sixteen years, I have carried the weight of being head of school. I don’t mean that grandiosely, I mean it as a felt experience. I’ve been on vacation--hiking in the mountains, walking through a market in a foreign country, trying to be fully present with my family—and known, always, that my phone could ring. That it could be anything. A death in the community. A lawsuit. A beloved teacher writing in late August to say they won’t be returning in the fall. Whatever it was, I was ultimately responsible. That is a weight, and it is also a privilege, and after long enough, it becomes something harder to identify: part of the architecture of your daily life. You stop noticing you’re carrying it. It’s just how things feel.

On July 1st, I will hand that weight to Tori. And when I try to imagine that moment, the emotion most present isn’t relief or grief, though I expect both. It’s something closer to disorientation.

For sixteen years, I have not just done the job of head of school. I have been the head of school. At the grocery store, in the carpool line, at a soccer game—people notice who I’m talking to, whether I leave at halftime. Not because of who I am, but because of the role I inhabit. Over time, the role and the self begin to merge. I think of conjoined twins sharing major arteries. Each has their own identity, but separating them is no easy feat.

The disentangling, I suspect, will be slow and strange. And yet the transition itself will happen all at once. On June 30th, I will be a head of school. On July 1st, I will not.

I’ll be living in a new city, in a community where many people will know me first as Rabbi Shira’s husband. I’ll be learning what days feel like without the laughter of children, what September feels like without the familiar cadence of a new school year.

I’m excited for what’s next. But I’d be lying if I said I know exactly who I will be when the role is gone. As I think about that, I realize I’ve spent years asking parents to do something remarkably similar. Not the head-of-school part, of course. But the work of loosening your grip on a role that has come to define you. The work of stepping back when we are biologically wired to step in.

Parents are always parents, even as the role shifts across a child’s life. Sometimes we struggle to evolve, or we’re driven by our own worries—about whether our child will be okay, or whether we are doing enough. I think of the parent who can’t stop checking in. The one who debriefs each test, each activity. The one who needs to be needed, and finds the slow loosening of their child’s dependence not just bittersweet, but somewhat destabilizing.

I often tell parents: this is what growing up looks like. Your job is to make yourself less necessary. It’s sound advice. It’s also really hard to follow.

That’s what Productive Struggle is about.

It’s about the gap between what we know and what we do. It’s about the moment at 11pm when the paper is due, the tears are falling, and the temptation to step in and fix it is almost unbearable. It’s about raising children who suddenly don’t need us as much as we need to be needed. It’s about learning to trust that struggle isn’t a sign that something has gone wrong, but instead a sign that something is going right.

I’ve watched this struggle play out for thirty years, in thousands of families, and I’ve lived it in my own. To be sure, I don’t have all the answers. But I’ve been thinking about these questions for a long time.

In this newsletter, I’ll write about what I’ve seen in schools, what I’ve lived as a parent, and what the research actually says about how children grow into capable, independent adults. Mostly, I’ll try to name the moments when we’re most tempted to step in, and what it might look like to step back instead.

I’m glad you’re here.