A Depressing Year Teaching High School Math

Jan 27, 2026 · 1158 words · Happened Jun 2000

I started my one-year stint as a high school math teacher around the summer of 2000, after I’d dropped out of the Michigan State University computer science grad program. The work I was doing there felt arcane and disconnected from the kind of life I wanted—I wanted something more real, more about people. I didn’t leave with a perfect plan, but I did have a lot of ideas.

Then my friend Lance—who I’d known since college at St. Andrews—told me Raleigh was desperate for math teachers. They needed people so badly they weren’t even requiring a math teaching degree. Lance was a math professor, living in Raleigh with his wife Erica, and he’d ended up teaching too.

The whole thing happened fast. I think the school had someone lined up, but it fell through, and I showed up about two weeks before classes started. I just walked in wearing a ratty T-shirt and shorts—definitely not interview clothes—and spoke with the principal. It felt like he just needed to confirm two things: that I was alive and that I could speak English. That was enough to get hired.

Suddenly I was at Leesville Road High School in North Durham, trying to prepare lessons while also figuring out a new city. There were meetings, a ton of prep, and I had to find a place to live. I got a one-bedroom apartment about a mile from the school—great location, but not lavish, and still more than I could really afford on a teacher’s salary. One saving grace was that Lake Lynn was directly down the hill from the apartment. The place didn’t have many amenities, but that lake was a real one: a loop trail, trees, water—something that looked like a life.

The first semester was hard, and the difficulty wasn’t the math. High school math itself wasn’t complicated; the real challenge was managing a room full of teenagers, grading, presenting, and handling the human side of the job. I taught Algebra 1, Part 1 and geometry. Algebra 1, Part 1 was basically a holding pen for kids who’d taken Algebra 1 and failed it—so now they were in an even more boring class that didn’t even count for their math credit. The message they were hearing was, you’re too bad at math to even do Algebra 1, and they knew it. A lot of those students weren’t motivated at all. Some weren’t planning on college and just wanted the diploma, and they’d tell me straight up they didn’t need this—like the kid who said he was going to work in his dad’s auto repair shop and didn’t need math, calling me Mr. Risk (which still sounds funny to me).

Geometry was a different world. Those students were generally more engaged, and the subject itself felt more visual and naturally interesting. My schedule ended up being three periods of Algebra 1, Part 1, then two periods of geometry. In a way it worked: I’d grind through the algebra classes and then feel like I got rewarded with geometry afterward. The first class was at 8 a.m., which helped because those kids were mostly half-asleep—if I could survive that one, the rest of the algebra periods often weren’t quite as bad.

Even so, that first semester hit me emotionally. I was 25, not much older than some of my students, which made authority tricky—I could slide into “older brother” territory if I wasn’t careful. I’d taught computer science at St. Andrews before, so I went in thinking teaching would be similar, but it isn’t. College students are paying to be there; high school students are forced to be there.

Outside the classroom, I was alone. I didn’t know anyone in Raleigh, I lived by myself, and when I had a bad day I just had to absorb it with no real support. I’d work through some of the stress of the day by running or rollerblading around Lake Lynn, doing loop after loop until my head cleared out enough to go back to the apartment. And I tried, in that early-internet way, to shake the loneliness by getting on what I think were the earliest forms of online dating: Yahoo Date. It was basically all text-based. Almost nobody had the courage to upload a photo because of the now-ridiculous fear that someone would use it to track you down and murder you. I’d spend hours messaging people, sometimes even have a promising phone call, and then watch it fizzle in person. None of it fixed the underlying thing, which was that my actual day-to-day life contained very few human moments that weren’t me standing in front of a classroom.

I seriously considered quitting after that first semester.

During Christmas break I decided to rally and make changes. I taught in a trailer outside the main building, and it had this feeling like darkness hung in the corners. It smelled like years of chalk dust, mold, and human. The carpet was a depressing brown; the walls were depressing dark-brown wood paneling. The chalkboard had ghost etchings from years of use, the kind of faint white scratches that never really come out no matter how much you erase. The whole room felt dark and dead.

So I pulled the blackboards down and put up white shower board so I could use it as dry erase boards. I added extra lights, brought in artwork, nailed a little shelf to the wall, and put a CD player on it. I started playing soft classical music or soft jazz at a very low volume. The effect was intentional: when there’s soft music, the room’s “conversation level” tends to drop, because students have to quiet down to hear it. Without music, the silence gets filled by noise, and the whole room can turn into a rabble.

When the students came back, it felt like a reset—partly because Christmas break is a reset on its own, and partly because the classroom environment had changed so much. The teacher-student rhythm improved too; we’d learned how each other worked. Some kids who were really problematic in the first semester eventually became some of the better ones later on.

By the end of the year, I’d settled into the teacher role more, and things were relatively smooth. Still, it felt like both the administration and I had the same conclusion: that was a fun little experiment, let’s not do this again. Moving my stuff out of the classroom trailer, it was raining while "Why Does It Always Rain on Me?" by Travis played, which felt fitting. After that year I moved on, and that summer I ended up taking a job at the Cat’s Cradle.

The biggest lesson I carried out of that year wasn’t really about teaching—it was about loneliness. Living alone in a city where I didn’t know anyone, teaching a subject most people disliked, I got a taste of what people now call the loneliness epidemic. One depressingly funny detail is that I’d play an Adam Sandler comedy CD in my apartment just to hear human voices—just to create the simulacrum of companionship.