It came up in a conversation about next year.
Nothing serious. Nothing emotional.
We were talking about plans that would stretch beyond the current school year—staffing, a few things we wanted to improve, something that would probably take two or three years to properly settle.
Someone said, almost casually, “Well, you’ll still be here.”
I smiled.
“That’s the plan.”
The conversation continued.
But something about my answer stayed with me.
Not because it was dishonest. As far as I know, I will still be here.
What bothered me was the question that arrived immediately afterward.
Do I want to be?
Nothing happened
That’s the difficult part to explain.
Nothing happened.
There was no terrible meeting that made me walk back into my office and start looking for another job.
No parent finally pushed me too far.
No teacher said something unforgivable.
No supervisor made an impossible demand.
No scandal. No public failure. No moment when I threw my hands up and thought, That’s it.
If anything, things are reasonably fine.
The school is functioning.
There are problems, of course. There are always problems. But there are also good people here. Teachers I respect. Students I care about. Staff members who work incredibly hard.
There are days when I walk around the school and feel proud of what we’ve built.
There are moments when someone tells me that something we changed is working, or a teacher I encouraged succeeds at something they weren’t sure they could do, or a student stops to tell me something completely ordinary about their day.
Those moments still matter to me.
I’m not failing at this job.
And perhaps that’s why admitting this feels so uncomfortable.
I think it would be easier to explain if I were.
If everything were falling apart, people would understand why I was questioning whether I wanted to continue.
But what do you say when you’re doing the job reasonably well and still find yourself wondering whether you want the job at all?
I wanted this
There was a time when becoming a principal meant something very different to me.
I saw it as growth.
An opportunity to influence more than my own classroom. A chance to shape a school, support teachers, make decisions that could improve things for students.
I worked for it.
I prepared for it.
I imagined it.
And when the opportunity finally came, I was proud.
My family was proud too.
There are teachers who would love to have this opportunity. People studying, preparing, applying, waiting for their chance.
I know that.
Which makes the thought feel almost ungrateful.
How do you work so hard to get somewhere and then quietly wonder whether you still want to be there?
Sometimes I catch myself trying to build a case against my own feelings.
You’re lucky.
You worked for this.
You’re good at it.
People trust you.
You can make a difference here.
All of those things may be true.
And somehow they haven’t made the question disappear.
I don’t think it was one thing
I’ve tried to identify when this started.
I can’t.
There isn’t a date I can point to.
I think the job simply became heavier in ways I didn’t notice while they were happening.
Not necessarily harder.
Heavier.
There is a difference.
It’s the number of things that stay in your head because they can’t always be said anywhere else.
It’s knowing the part of a situation that other people don’t know and then listening while they criticize a decision you cannot fully explain.
It’s walking into a conversation knowing that someone will probably leave disappointed.
It’s being asked, “What do you think we should do?” so many times that eventually you start wishing somebody else could decide something for you.
It’s having a day full of other people’s needs and then realizing at the end of it that you haven’t had much time to notice your own.
None of these things are extraordinary.
That’s probably the point.
They’re just part of the job.
And I knew the job would come with responsibility.
What I didn’t understand was how responsibility accumulates.
One decision doesn’t feel particularly heavy.
One difficult conversation doesn’t either.
One complaint, one deadline, one problem that follows you home, one situation you aren’t allowed to discuss freely.
You carry them.
Then another one comes.
And another.
You become very good at carrying things.
Eventually, people stop noticing that you’re carrying anything.
Sometimes you stop noticing too.
Maybe I’m just tired
I’ve asked myself that more than once.
Maybe this is simply a difficult stretch.
Maybe I need a proper break.
Maybe after some time away, I’ll come back and wonder why I ever questioned any of this.
Maybe there is one particular problem taking up too much space in my head and I’m confusing frustration with the job for frustration with the entire profession.
Maybe next year will feel different.
Maybe I don’t actually want to leave.
That’s possible too.
Because when I imagine no longer being principal, I don’t feel one clear emotion.
There is relief in the picture.
But there is loss too.
I think about the school continuing without me.
Someone else sitting in this office.
Someone else making the decisions.
Someone else knowing the things I’ve known and worrying about the things I’ve worried about.
I think about teachers I’ve worked beside for years.
Students I’ve watched grow.
Things we started that I would like to see finished.
There are parts of this work I would miss deeply.
That’s what makes the question difficult.
If I hated everything about being principal, the answer might be obvious.
I don’t.
I still care.
I still find meaning here.
I still have days when I know exactly why I chose this.
And I also have days when I wonder how much longer I want my life to feel like this.
Both things are true.
Being able to do it isn’t the same as wanting it
For a long time, I think I confused the two.
I kept asking myself whether I could continue.
Of course I can.
I can walk into school tomorrow.
I can answer the emails.
I can attend the meetings.
I can deal with whatever appears at my door.
I can make another difficult decision.
I can have the conversation I’ve been postponing.
I can prepare for another school year.
I know how to do this now.
But lately, another question has been sitting underneath that one.
Not:
Can I keep doing this?
But:
Do I want to keep living this way?
That feels harder.
Capability is easier to measure.
You can look at results. Feedback. What improved. What didn’t. Whether the school is functioning. Whether people trust your leadership.
Wanting is much quieter.
Nobody else can really measure it for you.
And perhaps that is why I’ve spent so much time trying to turn this into a problem I can solve professionally.
If I were struggling with a process, I could improve it.
If I lacked a skill, I could learn it.
If something at school wasn’t working, I could make a plan.
But I don’t know what plan you’re supposed to make for the possibility that the professional life you worked hard to build may no longer be the life you want indefinitely.
I kept waiting for a better reason
I think part of me believed I wasn’t allowed to question the job unless something sufficiently bad happened.
There should be an incident.
A breaking point.
Something I could explain when people asked why.
Instead, I have ordinary Tuesdays.
Calendars.
Phone calls.
Conversations.
Problems that get solved and are replaced by new ones.
Good days.
Difficult days.
And somewhere among all of them, this question has slowly appeared.
Perhaps that’s what I’ve found hardest to admit.
I don’t have a dramatic reason.
I don’t know whether I need one.
Tomorrow I’ll probably arrive at roughly the same time I always do.
I’ll put my things down.
I’ll look at what is waiting.
Someone will need an answer before I’ve finished the first thing I intended to do.
There will be emails.
There will be interruptions.
There will probably be something that makes me laugh.
There may be something that frustrates me.
Someone may walk into my office needing me to be the principal, and I will be.
I’ll do the job.
Probably quite well.
I still don’t know what I’m going to do about the question.
For now, I think I’m simply allowing myself to stop pretending it isn’t there.
Do I still want this?
When the question deserves somewhere private to go
Some questions about school leadership aren’t really about whether you’re capable of doing the job.
Sometimes the harder question is whether you still want the life that comes with it.
Should I Still Be A Principal? was written for school leaders who have reached that quieter, more complicated place. It doesn’t try to decide whether you should stay or leave. It gives you somewhere to examine what has changed, what still matters, what the position is asking of you, and what the different versions of your future might actually look like.
You don’t have to know the answer before you begin asking the question honestly.


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