My students, thirty years on

On Wednesday, I woke up early because I could hear the garbage truck and we’d forgotten to put out the bins. After I rolled them out to the curb, and as I made a cup of coffee, a name randomly popped into my head—a former student I hadn’t recalled in many years.

I wondered where she ended up. On LinkedIn, I discovered she’s working as a freelance writer and editor in New York. I remember her as a yearbook staff member and student in my creative writing class. Good for her, I thought.

And then, as one does when it is a rainy day, the office is closed, and one’s teenage children will be asleep for five more hours, I descended into a giant internet rabbit hole.

It started by looking up a few more of her classmates and then it mushroomed into: “Wouldn’t it be something to look up all the members of the Class of 1996?” And so, with their yearbook to supply the names, I did. (Mercifully, it was a small school.)

This class started high school the same year I started teaching. They were 14 and I was 22, a gulf in age and experience that seemed meaningful then and is meaningless now. Thirty years later, they’re in their mid-40s.

I taught them English, biology, and creative writing. I was their class sponsor, and when they graduated I did too, leaving to get my masters degree at UVA.

I paid two of my students to help me move all my stuff from Winchester to Charlottesville. One had grown a giant beard and I worried he would pass out in the August heat. The other I called “Pepper Boy” because of a Saturday Night Live skit we both found hilarious.

Pepper Boy was a wrestler who quoted T.S. Eliot and edited our school literary magazine. He’s now raising two boys and working with unhoused people at the regional community services board. His good friend, the bearded mover, leaves a lighter internet footprint but I believe he’s now managing a convenience store in their hometown. I remember them both with great affection. Others in that writing class work for Winchester Parks & Rec, Microsoft, and Dominion Energy. One heads up user experience design at a firm in Paris, one manages a Taco Bell, and one performs his own original bluesy folk music.

I found out that the young people I taught 30 years ago are now pulmonologists, cosmetologists, teachers, fundraisers, construction managers, lawyers, electricians, pharmacists, and store owners. Two sell Toyotas and one sells Ferraris. Before she sold luxury cars, I knew her as the student talented in art and shot put who arrived early to school so she could walk the halls with me and talk about troubles at home.

Some of the paths they took don’t surprise me: the student passionate about music and drama now manages theater programs at the Shenandoah Conservatory. Another who was a gifted pianist and singer now plays organ and conducts a choir in upstate New York.

I’m not at all surprised to see that the athlete voted “Most Popular” his senior year is now serving on City Council, nor that the responsible and likeable yearbook editor chose a career in Human Resources.

Two close friends from the tonier part of town now own a fine art gallery and organize galas and events in Virginia’s Hunt Country.  A former Latin scholar and Young Republican is now a conservative columnist who pens a newsletter called “Notes from the Right”. Various other Young Republicans went to UVA, became venture capitalists, and will retire before I do.  

I sponsored the Young Democrats club, which in Winchester meant rooting for the underdog.  The young woman I remember as our most outspoken and wholehearted member, with a wild cloud of curly hair, is now a close-cropped professor at Carnegie Mellon. The club’s president became Obama’s Special Assistant and House Legislative Affairs Liaison.

One of the happiest stories, at least to me: My student who grew up in the city’s residential children’s home is now a mother and an emergency room doctor in another state. I knew her as a soft-spoken sophomore, a copious notetaker when we read Native Son, and a Howard University hopeful. That she’s gone so far, figuratively and literally, is a delight but not a surprise.

Others, however, did deliver some surprising plot twists. The student I was sure would take over his family’s funeral home opted instead to become a tennis pro and then a digital marketer. A school security guard in Loudoun County with extra time during the COVID shutdown switched careers and now she’s a personal trainer. A hospital security guard went on to earn his license as a private investigator and later changed jobs again: he’s now a lead data center design engineer, a job none of us knew anything about in 1996.

​One student who listed no high school activities beside his yearbook senior portrait went on to have a career that’s hard to encapsulate: it involves army service in Oslo, Paris, South Korea and the Gulf of Guinea; co-founding a startup that creates wearable technology for elderly people and their caregivers; co-leading a crowdsourced forecasting project on the security and policy implications of AI; and now advising at a climate communications and consulting agency.

Another surprise involves a student named Sam. At the high school where I taught, every year the eleventh graders stockpiled funds for their senior prom by operating the football concessions stand. The year it was my class’s turn, the football team enjoyed an interminably long season that stretched nearly to winter break: we kept warm by boiling literally thousands of hot dogs. Yesterday I searched online for Sam, a student I associate with that bone-chilling but very lucrative experience; I found him only after I realized he now goes by his middle name. He has the very cool-sounding job “Vice President of Memorabilia and Design” for Hard Rock International, overseeing the largest collection of music and entertainment memorabilia in the world.  

Students in this class have been in rehab centers and psychiatric hospitals. One now lives in a nursing home after a youthful prank led to a terrible accident and brain damage. Two have gone to prison for dealing cocaine and breaking and entering. Two have died: one was a bank manager who was better known to the business teachers at the high school, and the other was a student of mine. I remember his clever sense of humor, his gifts as a three-sport athlete, and his episodes of frustration as a special education student. He was buoyed by his resource teacher, his coaches, and his mother, who was an art teacher. I learned that he later served in the Navy and established a scholarship for aspiring artists graduating from high schools in the Shenandoah Valley. He died in 2021 at 43 and is buried next to the baby he and his wife lost five years earlier.


When I was their teacher, I never thought about my students being in their 40s. I rarely thought about them being 25. Maybe this was because I was so young (could I even envision myself in my 40s?) or maybe as a new teacher I was just focused on keeping one foot in front of the other.

Or maybe—and I think this is the strongest possibility—it’s because I was simply enjoying them in their present state. I loved their lack of self-awareness and their painful self-consciousness, their confidence and their awkwardness, their sense of triumph when they excelled and their hard-won composure in everyday defeats. I loved watching them try on adulthood. I was in no rush to hurry them along.

To be sure, it was my job to prepare them for what was next, as much as any of us could foresee what that meant. In education we talk about “college and career readiness” a lot.

​But looking back on it now, I think it also meant something to them (and to me) to enjoy them as they were, to convey to them the sense that they were people worth knowing. As a parent of high school students, I see what it does for my own kids when they’re able to build relationships with teachers who think highly of them and take pleasure in their company.

​I want that for everybody’s children, and I want that for every teacher. School board members are bit players in that story, but I hope my work on the board makes some difference. I’d like to think my small role makes it possible for other teachers to feel as alive as I did when I was in the classroom, and for their students to be certain they are people worth knowing, today and thirty years on.