The Decisions That Stay With You – Even the ones you got right.
There is a particular kind of tiredness that has nothing to do with the hours you worked.
It arrives later. Often at night, when the building is closed and the day should be finished.
A decision from weeks ago surfaces, uninvited. Not the big, visible ones - those get reviewed, written up, defended in meetings. It's the smaller one. The conversation you ended a certain way. The plan you chose over another plan. The moment you said yes when part of you wasn't sure, or said no and have wondered about it since.
It doesn't shout. It just stays.
This is the part of the year school leaders rarely talk about. July arrives, the building empties, and you're meant to feel some kind of release. Instead there's often a quieter, more private accounting - a slow walk back through everything you decided this year, looking for the moments that still feel unfinished.
You think about the family you reassured, hoping it was the right call. The colleague you supported one way rather than another. The timetable, the structure, the policy you held to, even when it cost something. Each one made with care, in the time you had, with the information you had. And still - some of them stayed with you longer than you expected.
This is what it means to lead people, not just systems. A system doesn't keep you up at night. A person does. A choice that touches a child, a family, a colleague's working life - that kind of decision doesn't close cleanly just because the school year does.
There's a reason this lingers the way it does. You care about getting it right. Not approval - right. The decisions that stay with you are very rarely the ones you didn't care about. They're the ones where you did, and where "right" wasn't simple, and where you had to choose anyway.
And here is something worth saying plainly: most of you, doing this work, still love it. The overthinking isn't evidence that the job has become too much to bear - it sits right alongside the parts that still feel like purpose. The moment a pupil came back to thank you for something you'd half-forgotten. The colleague who's grown into themselves under your watch. The quiet pride of a school that runs because of decisions you made, even the imperfect ones. The weight and the meaning are often standing in the very same place. That's not a contradiction to resolve - it's simply what this kind of leadership is made of.
But the weight is still real, and it deserves to be named instead of pushed past.
End of year reviews ask you to look back at outcomes - results, targets, what was achieved. They rarely ask what it cost you to get there, or which decisions you're still turning over. There's a particular kind of loneliness in carrying that privately while the official version of the year gets reduced to a summary on a slide.
Somewhere in every leadership year there's a fork - a moment where two paths were both reasonable, and you could only walk one. You chose. The other path doesn't disappear just because you didn't take it. It sits there, quietly, as the version of the decision you'll never get to test. That's often what stays with you longer than the decision itself - not regret exactly, but the not-knowing. The other path you'll never walk.
You can probably name a few of these forks without much effort. The structure you chose for a team, knowing another shape might have served someone better. The way you handled a difficult parent meeting, replaying afterwards whether a different tone might have landed more gently. The appointment you made, the one you didn't, the difficult conversation you finally had in March that you now wonder should have happened in October. None of these were careless. All of them were chosen by someone trying, in real conditions, to do right by people who were relying on them.
It would be easier if leadership worked the way scorecards suggest - right or wrong, resolved by results. But most of the decisions that matter aren't like that. They're made in real time, with partial information, under pressure, for people who deserve care. Getting everything right was never actually on offer. What was on offer was doing your best, with what you knew, in the moment you were in.
There's also a particular shape this takes for school leaders specifically, that's worth naming. The school year has an unusual rhythm - a hard stop in July, followed almost immediately by the start of planning for September. There isn't much real distance between "the year that just ended" and "the year about to begin." So the review and the rebuild happen almost on top of each other, and the decisions you're still processing from last year are sitting right alongside the decisions you're already starting to make for next year. It's no wonder some of it never quite gets put down.
That doesn't make the late-night replay disappear. But it might change what you do with it.
This is the part of leadership no one prepares you for - not the deciding, but what you do with a decision afterwards, once it's already made and can't be unmade.
If any of this feels familiar, there may be something gentle to notice…
1. Write an unsent letter to yourself - from this point in the year, to the version of you who made one of the decisions still sitting with you. Say what you'd want them to know.
2. Name three values that were present in a difficult decision this year, even if the outcome still feels unresolved. Notice that the values were there, whatever happened next.
3. Before the year is filed away, choose one decision you're still carrying and ask: what did I know at the time? Not what you know now - what you knew then. Let that be enough, even briefly.
4. Think of the path you didn't take in one of those forks. Notice whether you're still trying to prove that path wrong, and what it might feel like to simply let it stay unknown.
5. Notice one decision this year that you'd make exactly the same way again, knowing everything you know now. Let yourself sit in that for a moment, without rushing past it.
6. If you're already planning for September, notice when last year's unfinished business quietly slips into this year's planning. You don't have to solve it - just notice the overlap.
7. Think of one person this year who is better off because of a decision you made. Let that sit alongside everything else you're carrying, rather than separate from it.
Some decisions close on their own, in time. Others simply become part of what you carry into the next year, a little lighter for having been named rather than buried.
The path you didn't take is not a verdict on the one you did.
I help school leaders who feel like they’re slowly disappearing into the job -
find their way back.
If this resonates, I offer a complimentary 30 ‑ minute session where we focus on one thing that’s on your mind.
A simple space to step back, think clearly, and begin to feel like yourself again.