Why I Stopped Feeling Guilty for Leaving Teaching

There's a kind of teacher guilt that nobody talks about enough.

It's not the guilt of losing your temper with a student, or missing a deadline, or not being able to reach the kid in the back row no matter what you tried. Those are the guilts teachers talk about in staff rooms and on Reddit threads.

The guilt I'm talking about is quieter and worse: the guilt of wanting to leave.

I had it for two years before I actually left. Two years of drafting LinkedIn messages to recruiters and then not sending them. Two years of taking professional development courses on nights and weekends and feeling simultaneously excited and ashamed. Two years of asking myself: what kind of person who genuinely loves teaching just decides to stop?

I'm writing this because I've since talked to dozens of teachers in various stages of this same process, and almost every one of them describes the same internal experience. The guilt is universal. And the story most people tell themselves to explain it — that leaving means you didn't love it enough, or you gave up, or you're betraying the kids who needed you — is almost always wrong.

The story I told myself

My version of the story was very specific. I taught eighth grade English for nine years in a Title I school. I had students who came back to visit me years after graduation. I had parents who called me in October to make sure their kid was in my class. I was, by most external measures, a good teacher who mattered to people.

So when I started thinking seriously about leaving, the story I told myself was: "Only people who aren't really invested leave. If you were really committed to the kids, you'd stay."

I held that story for a long time. Too long.

The reframe that changed everything

It came from an unexpected place — a conversation with an edtech founder who had also been a teacher. She said something I've thought about almost every day since:

"A teacher reaches 150 students a year. A product that works reaches 150,000. If the product actually understands classrooms — which it can only do if someone who built it actually taught — then leaving the classroom isn't abandoning students. It's scaling your impact by three orders of magnitude."

That's not a rationalization. It's a different way of thinking about what education actually needs.

The $340 billion edtech industry is largely being built by people who have never taught. Who have done "user research" with teachers — which means they watched a few teachers for an hour, maybe ran a focus group — and then built a product based on what they think the classroom experience is like.

The result is most of the tools you've been forced to use. The ones that add steps instead of removing them. The ones that create data instead of saving time. The ones that look impressive in a purchasing committee meeting and fall apart on day one of actual classroom use.

What actually happened when I left

I spent the summer learning to build things. I started with the worst parts of my own classroom experience — the ones I'd been complaining about for nine years — and I tried to build something that solved them.

It was hard. I didn't know what I was doing. But I had something no bootcamp graduate had: I knew exactly what problem I was solving, and I knew it from the inside. I knew what teachers actually wanted versus what they said they wanted in surveys. I knew where the real friction was. I knew which workflows were irreplaceable and which ones were just habits nobody had questioned yet.

That knowledge is worth more than most people realize. And the tech industry is starting to figure that out.

If you're in the middle of this

I'm not going to tell you to leave teaching. I don't know your situation. I don't know which students are counting on you this year, or what you'd be leaving behind.

But if you're in the middle of the guilt — feeling the pull toward something different and also feeling like you shouldn't want it — I want you to know that the guilt is not a sign that you made the wrong choice. It's a sign that you cared about the right things for a long time. Those two things can coexist.

And if the pull you're feeling is toward building things, toward using your understanding of classrooms to make better tools for the teachers and students who are still in them — that's not abandonment. That's a different kind of commitment to the same mission.