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.
