Dear The Good Principal,
I’m not even sure why I’m writing this tonight.
I was scrolling through your confessions and read something that reminded me of how things used to be when I was still teaching in the classroom.
And then I started thinking about things I haven’t thought about in years.
I’ve wanted to tell someone about this, but I’m worried people might misunderstand me. Especially those who know how hard I worked to get where I am now.
So maybe it’s easier to say it here, where nobody knows who I am.
You can call me Helen.
I would really like to hear from other school leaders who have been in this position. Maybe I’m just being sentimental. I don’t know.
I wanted this role.
That is important.
I applied for it. I prepared for it. I was proud when I got it. My family was proud too.
And I still care about the work.
So this is not a resignation letter disguised as a confession.
At least I do not think it is.
But a few weeks ago, I stopped outside a classroom and watched a teacher doing a reading activity.
Nothing special was happening.
No award-winning lesson.
No big school event.
Just children talking, laughing, putting their hands up, getting answers wrong, trying again.
And something in me just stopped.
I stood there longer than I needed to.
Then I had a thought that felt much heavier than it should have.
I miss this.
That is where this started.
I passed by a classroom last week and stopped for no reason.
Well…
there was a reason.
The teacher was doing a reading activity and the kids were completely into it. Hands up. A little noisy. Someone laughing at the wrong answer. Someone else trying very hard to be picked.
Normal classroom stuff.
I stood by the door for maybe a minute.
Then I had this thought I haven’t said out loud before.
I miss this.
Not the paperwork.
Not the lesson plans.
Not the checking.
Not the days when half the class forgot what you literally taught yesterday.
I miss being responsible for one room.
One group of kids.
One lesson at a time.
That sounds almost stupid now because when I was still teaching, I remember complaining too.
Of course I did.
I complained about reports.
Parents.
Deadlines.
Meetings.
Behavior.
Everything.
I remember thinking becoming a principal would mean I could finally do something bigger.
More impact.
More influence.
More say.
And yes, that part is real.
I do have more say now.
I also have more of everything else.
More people.
More problems.
More things I cannot walk away from.
That’s the part I didn’t fully understand.
When I was a teacher and something went wrong in another classroom, I could care about it without being responsible for fixing it.
Now?
Eventually it finds me.
A teacher has an issue.
A parent complains.
A student concern gets bigger.
A schedule collapses.
Someone is absent.
Someone is angry.
Someone needs approval.
Something from the district lands in the inbox.
And somehow it all starts pointing in the same direction.
My office.
Sometimes I miss having a door I could close at the end of the day and know the class was done.
Not perfect.
Not finished forever.
Just done for today.
There was a boundary.
Bell rings.
Students leave.
You clean up.
Maybe you bring work home, sure.
But the room goes quiet.
Leadership doesn’t really go quiet in the same way.
Even when the school is empty, there is usually something waiting.
An email.
A message.
A decision.
Something tomorrow.
Something you forgot today.
I was watching that class and one of the students noticed me.
“Ma’am!”
Then everyone looked.
Great.
So I smiled and walked in.
The teacher laughed and said:
“Ma’am, do you want to take over?”
She was joking.
I almost said yes.
Actually…
for about five seconds I really wanted to.
Just give me the book.
Give me the lesson.
Give me twenty-five students and one objective.
Let me worry about whether they understood the story.
Let somebody else worry about everything else.
I didn’t say that.
I said:
“No, no, continue.”
Then I stood there for a few more minutes.
One student gave an answer that was completely wrong but said it with so much confidence that everyone laughed.
I laughed too.
And I realized I missed that kind of problem.
Wrong answer.
Try again.
Simple.
Not easy.
But simple.
There is a difference.
A classroom can be hard.
Really hard.
But most of the time you know what you are trying to do.
Teach this.
Help this child.
Finish this lesson.
Tomorrow, try again.
As principal, sometimes I finish the day and I’m not even sure what the main thing was.
Was it the parent?
The staff issue?
The report?
The teacher who came in upset?
The student concern?
The district deadline?
All of it?
Some days the job feels like being pulled in ten directions and calling that leadership.
And then I feel guilty for missing teaching.
Because this is what I worked toward.
I wanted this.
I applied.
I prepared.
I was happy when I got the position.
People congratulated me.
My family was proud.
I was proud too.
So what exactly am I supposed to do with the fact that sometimes I miss the life before it?
I don’t mean I want to go backward.
At least…
I don’t think I do.
That’s where it gets uncomfortable.
Because some days I know I’m just tired.
I miss the classroom because the office is exhausting.
That makes sense.
But other days?
I wonder if I actually miss who I was in the classroom.
I miss talking to children more than adults.
I miss making something.
A lesson.
An activity.
A moment where a student finally gets it.
I miss knowing whether I had a good day.
Teaching gave me that sometimes.
A lesson worked.
A child improved.
The class laughed.
You knew.
Leadership feels less clear.
You can make the right decision and someone is still angry.
You can solve one problem and create another.
You can work all day and have nothing visible to show for it.
You can do your job well and still go home wondering if you handled something badly.
That uncertainty gets tiring.
A few days after that classroom visit, I found an old box at home.
Inside were some things from when I was teaching.
Old class pictures.
Notes students gave me.
A lesson plan I have absolutely no idea why I kept.
I sat there longer than I expected.
And I had that thought again.
I miss this.
Then another thought came right behind it.
Would I actually go back?
I don’t know.
That’s the truth.
I don’t know.
Part of me probably romanticizes it.
I remember the good things more clearly now because I’m not living the hard parts anymore.
If I went back to teaching tomorrow, give me two weeks and I’d probably be complaining again.
I know myself.
But still…
sometimes when I walk past a classroom, I feel something.
Not regret exactly.
Maybe longing.
Maybe envy.
Maybe just remembering.
And I think that’s what scares me a little.
Because “I miss teaching” sounds harmless.
But sometimes there’s another question hiding behind it.
Do I miss teaching… or do I not want this anymore?
I don’t know yet.
Maybe I don’t need to know yet.
But I’ve stopped pretending I never ask myself.
I think that is why I am writing.
I do not want someone to tell me to resign.
I do not want someone to tell me to be grateful for the role either.
I suppose I just want help understanding what this feeling means.
Is it normal to miss the life you had before leadership even when you chose leadership willingly?
Can you miss teaching deeply and still genuinely want to remain a principal?
And how do you know when nostalgia is just nostalgia…
and when it is starting to tell you something about what you actually want next?
I would really like to hear what The Good Principal thinks.
And if other school leaders have ever stood outside a classroom and felt that little pull back toward the life they used to have, I hope they say so too.
Thank you for giving us somewhere to ask questions we are not ready to answer yet.
— Helen
FROM THE GOOD PRINCIPAL’S OFFICE
Helen, I would start by taking some pressure off the question.
Missing teaching does not automatically mean becoming a principal was a mistake.
That is important.
Sometimes we treat longing as evidence.
It is not always.
You can miss an old part of your life without wanting the whole life back.
You can miss the classroom and still value the work you are doing now.
You can miss the person you were as a teacher without necessarily wanting to resign from leadership.
And sometimes we miss something simply because the part we are living now is hard.
That does not make the feeling fake.
But it does mean the feeling deserves a little more examination before it becomes a conclusion.
What I think is especially important in your confession is what exactly you miss.
You did not say:
“I miss grading papers.”
You did not say:
“I miss classroom behaviour problems.”
You did not say:
“I miss lesson plans and parent messages and all the things that exhausted me when I was teaching.”
You said you miss:
one room,
one group of students,
one lesson,
a clearer sense of what you were trying to accomplish,
and the feeling that at the end of some days, you could actually tell whether something worked.
That tells us something.
Maybe what you miss is not teaching as a job.
Maybe you miss proximity.
The impact was closer.
You could see it.
A child understood something she did not understand twenty minutes earlier.
A student who had been struggling finally raised her hand.
A lesson clicked.
The class laughed.
You knew what the moment meant.
Leadership impact often happens farther away.
You make a staffing decision and maybe the effect is visible months later.
You support a teacher and that teacher eventually does something wonderful with students, but you may never see the exact moment your support mattered.
You resolve a conflict and success looks like nothing else happening.
You improve a system and eventually everyone forgets how bad the old system was.
Leadership success can be strangely invisible.
That difference matters.
You may not be missing the classroom because you want to leave leadership.
You may be missing the feeling of seeing your work land somewhere immediately.
That is worth knowing.
There may be ways to bring some of that back into your current role.
Not as a trick to keep you in the principalship.
Just because the part you miss may still have a place in your life.
Spend time in classrooms that is not only observation.
Read with a group occasionally if your context allows it.
Join an activity without turning it into supervision.
Talk to students when there is no problem to solve.
Keep some contact with the part of education that made you want to be in schools in the first place.
Sometimes leaders spend so much time managing the organization that they become disconnected from the thing the organization actually exists for.
Students.
Learning.
Teaching.
That disconnection can make the role feel much more administrative than meaningful.
But there is another part of your confession that deserves more attention.
You asked:
“Do I miss teaching… or do I not want this anymore?”
That is a different question.
And I would not rush it.
Because nostalgia can become very persuasive when you are tired.
The past gets edited.
You remember the student who finally understood the lesson.
You do not always remember the marking pile.
You remember laughing with the class.
You forget the parent email that ruined your evening.
You remember having one classroom.
You forget what it felt like when that one classroom was completely exhausting.
That does not mean your memories are false.
It means they are incomplete.
So if you are seriously considering what you want next, compare real life to real life.
Not the hardest version of the principalship against the highlight reel of teaching.
Ask yourself:
What exactly do I miss?
The students?
The daily rhythm?
The creativity?
The direct feedback?
Less organizational responsibility?
A clearer end to the day?
The identity of being a teacher?
Once you know what you are actually longing for, the question becomes more useful.
Because different longings suggest different possibilities.
If you miss students, maybe you need more direct contact with them.
If you miss teaching itself, maybe that deserves deeper thought.
If you mainly miss having less responsibility, then the issue may not be teaching at all.
You may simply be exhausted by carrying too much.
If you miss who you were then, perhaps the question is whether leadership has crowded out parts of yourself you want back.
And if, after all of that, the thought still remains:
I genuinely think I would rather teach again,
that is also information.
It does not make the years in leadership a failure.
A career does not have to move in one direction forever.
Promotion is not a one-way door.
Sometimes people change.
Sometimes what mattered at forty is different at fifty.
Sometimes you get the role you wanted and eventually discover you want something else.
That can be uncomfortable because leadership positions often become wrapped up in identity.
Going back to teaching can feel like going backward.
But professionally speaking, those are not necessarily the same thing.
Moving to a role that fits the life you now want is not automatically regression.
Still, I would not make that decision from one nostalgic classroom doorway.
Give the feeling time.
Watch the pattern.
When does it show up?
Only after brutal leadership days?
Or even after good ones?
When you imagine returning to teaching, do you feel relief because you want to escape something…
or genuine energy because you want to move toward something?
Those are different.
Ask yourself another difficult question:
If the principalship became more manageable tomorrow, would I still want the classroom back?
That can help separate exhaustion from desire.
And maybe another:
If I could keep the parts of leadership I value but remove the parts currently wearing me down, would I still want to leave?
Again, not because there is a correct answer.
Because sometimes we say:
“I want to go back.”
when what we really mean is:
“I cannot keep doing it like this.”
Those are not the same sentence.
And this is one of those situations where I can genuinely say:
there is a book for that question.
Should I Still Be A Principal? was written for school leaders who have not necessarily decided to leave but have started asking questions they can no longer dismiss.
Not:
“How do I become a better principal?”
A different question.
“Do I still want this?”
And underneath that:
Do I dislike the principalship?
Or this particular season?
Am I exhausted?
Or have I changed?
Do I want to leave leadership?
Or do I simply need leadership to take a different shape?
Am I remembering teaching realistically?
Or am I reaching toward the last version of my professional life that felt simpler?
What would staying cost?
What would leaving cost?
What life do I actually want around the work now?
The book is not there to persuade you to stay.
It is not there to make returning to teaching sound like failure.
And it does not assume that questioning the role means you are already halfway out the door.
It simply gives the question somewhere to go.
Because sometimes the most important thing is not answering:
“Should I still be a principal?”
immediately.
Sometimes the first step is finally admitting:
“I am asking.”
That is where you seem to be, Helen.
And I think that is enough for now.
You do not need to turn one moment outside a classroom into a career decision.
But you also do not need to laugh it off simply because you worked hard to become a principal.
You are allowed to examine the life you wanted…
now that you know what actually living it feels like.
Maybe you will discover that you still want it very much.
Maybe you will discover that something about the role needs to change.
Maybe one day you will choose something else.
None of those answers has to be decided today.
For now, keep paying attention to the feeling.
Not fearfully.
Curiously.
And if the question keeps returning, Should I Still Be A Principal? may be worth opening.
Not because it already knows the answer.
Because it was written for the school leader standing exactly where you are:
between:
“I miss what I had.”
and
“I’m not sure what I want next.”
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