If You’ve Seen One Jewish School, You’ve Seen…One Jewish School

Like many Canadians, this December took me from snowy boots to sandy flip-flops as I spent time in Florida. What I encountered there—sometimes in the span of a single day—was a striking reminder of the diversity, complexity, and quiet miracle of Jewish day schools, and what that diversity asks of us as leaders.

Like many Canadians, this December took me from snowy boots to sandy flip-flops as I spent time in Florida.  However, what made this trip different was not the weather, but the work: over the course of a few days, I had the opportunity to visit several Jewish day schools in person, sometimes more than one in the same day.

What struck me wasn’t simply the warmth or the hospitality.  It was the contrast.

In the span of hours, I moved between schools that differed dramatically in size, educational philosophy, religious culture, physical space, and communal norms.  Different buildings.  Different dress.  Different rhythms of tefillah and learning.  Different assumptions about what a “good day school” looks like.  And yet, each was deeply and unmistakably Jewish – animated by care for children, commitment to Torah, and responsibility for the future.

I found myself thinking: this is a quiet Jewish miracle.

We often talk about “diversity” in Jewish education, but usually in abstract or ideological terms – denominations, movements, labels.  What I witnessed instead was diversity as it actually lives and breathes: in hallways and classrooms, in schedules and staffing models, in the daily choreography of institutions serving real families in real communities.

And this was just one small slice of a much broader tapestry.

In my current work, I’m in relationship with schools across continents and across the Jewish spectrum – large and small, legacy institutions and newer ones, schools wrestling with growth and schools wrestling with sustainability.  The contexts vary widely.  The challenges don’t always rhyme.  And the solutions cannot be imported wholesale from one place to another.

Which is precisely the point.

Strong ideas matter.  Research matters.  Proven practices matter.  But they only become transformative when they are translated and interpreted through local culture, capacity, and readiness.  Too often, we confuse replication with leadership, assuming that what worked “there” will work “here,” if only we apply it faithfully enough.  In reality, systems fail not because ideas are weak, but because context is ignored.

This is where humility becomes a leadership skill.

Not the performative kind, but the disciplined kind: the willingness to listen before prescribing, to ask better questions before offering frameworks, and to assume that wisdom already exists within the institution, even when outside expertise is invited in.

January is a funny month in schools.  Some communities are just regaining momentum after Winter Break; others are easing toward Yeshiva Break.  It’s a liminal time—part reset, part continuation.  It’s tempting to think of this stretch as lost time, or as a holding pattern before the real work begins.

I’m increasingly convinced the opposite is true.

These in-between moments are where the most important noticing happens.  What feels heavy right now?  Which conversations are being deferred?  What successes deserve more attention than they’re getting?  The experiences leaders are having now are often the clearest signals of the changes they’ll want to make later – but only if they pause long enough to name them.

I’ve long believed in taking advantage of all the “new years” available to us: the secular new year, Rosh Hashanah, Pesach, Tu BiShvat.  Each invites a different kind of stock-taking.  Each creates space not just to set goals, but to revisit assumptions.

So, in that spirit, here are a few quiet “resolutions” I’m carrying into the (secular) year ahead shaped by what I’ve seen recently, and by the privilege of walking alongside many very different schools:

  • To keep difference visible rather than smoothing it over in the name of efficiency or scale.
  • To lead with questions before frameworks, and curiosity before conclusions.
  • To resist one-size-fits-all solutions, even when they are elegant or popular.
  • To honor the wisdom already present in institutions, not just the expertise brought from outside.
  • To remember that meaningful change depends as much on readiness and relationships as it does on strategy.

Jewish day schools do not form a single story.  They are a library of stories – distinct, contextual, and deeply rooted.  The work ahead is not to unify them into sameness, but to help each one become more fully itself, in service of the children and communities it serves.

Standing in Florida classrooms in December – moving from boots to flip-flops, from one world to another – I was reminded how rare, fragile, and hopeful this ecosystem really is.

That feels like the right place to begin the year.

Starting Early Enough to Do It Right

The hardest thing to do – even when you know it – is to start early enough to do it right. As schools head toward Chanukah and Winter Break, a reflection on leadership, time, and why the work we are living now must shape the change we hope to make next.

One of the things I say most often in my leadership coaching is also one of the hardest things to live by:

The first day of school is the beginning of the planning for the next school year.

Intellectually, most Heads of School know this. Practically, almost none of us experience it that way.

Instead, the first day of school is the beginning of…everything.  Counseling out a student who clearly isn’t thriving.  Offering difficult feedback to a teacher you genuinely care about.  Celebrating a small but meaningful success that took far more effort than anyone realizes.  Sitting with a family in pain.  Feeding Jewish souls.  Managing the thousand invisible decisions that make a school function before lunch.

And all of this unfolds inside the same, stubborn reality: time is a zero-sum game.  Every hour spent responding to what’s urgent feels like an hour stolen from what’s important.  Even when we know better, the hardest thing to do is to start the things early enough to do them right.

In theory, we want to plan.  (Man plans.)

In reality, life intervenes.  (God laughs.)

What I’m seeing again and again in my coaching work is not a lack of insight or commitment among school leaders.  Heads know what they want to change.  They know what’s not working.  They know where systems are misaligned, where culture needs tending, where capacity is stretched too thin.

What they lack is not vision.

It’s space.

The paradox is this: the experiences you are having now fuel the changes you are craving for the future.  The tensions of October.  The hard conversations of November.  The exhaustion of December.  These are not distractions from the work – they are the work.  They contain the data, the stories, and the emotional truth that should shape what comes next.

But here’s the rub: you cannot build that bridge later if you don’t begin laying it now.

Starting early doesn’t mean drafting a strategic plan in September or adding another initiative to an already overflowing plate.  It means noticing. Capturing.  Naming.  Asking better questions while the experience is still alive:

  • What patterns am I seeing right now that I don’t want to normalize?
  • Which decisions feel reactive—and why?
  • Where are people asking for clarity that I’m not yet giving?
  • What am I learning about our systems, our culture, our limits?

This is the quiet work before the work.  And it’s the part that gets skipped most often – not because leaders don’t value it, but because it doesn’t scream for attention the way today’s crisis does.

The danger in waiting is not just that we lose momentum.  It’s that by the time we’re finally “ready” to plan, the experiences that should have shaped our thinking have already been flattened into memory.  We remember the conclusions, but not the texture.  The emotion.  The human cost.  The nuance.

As we head into Chanukah, many schools are cresting toward Winter Break—or, in some communities a bit later, Yeshiva Break.  There is a familiar rhythm to this moment: exhaustion mixed with pride, relief paired with a quiet sense of unfinished business.  We tell ourselves that the pauses ahead will give us space to think, to plan, to reset.

Sometimes it does.  Often, it doesn’t.

Breaks offer rest – which is essential – but they rarely offer clarity on their own.  By the time January (or February) arrives, the pace returns quickly, and whatever we hoped to hold onto from the fall can feel strangely distant unless we have already begun to notice it with intention.

So perhaps the invitation for this moment is a modest one.  Not to solve, fix, or design – but to begin.  To capture what you’re seeing now while it’s still vivid.  To write a few notes you won’t yet act on.  To name the questions that deserve more time than you currently have.  (Perchance to blog?)

Starting early doesn’t mean starting loudly.

It means starting honestly.

The first day of school really is the beginning of the planning for the next school year.  Not because we should rush, but because the story is already being written – whether we are paying attention or not.

Chanukah reminds us that light doesn’t come from certainty.  It comes from beginning, even when the oil doesn’t yet feel like enough.