Tomorrow is the first day of my seventh year teaching online.
Last night, I sat at a graduation party for a former student, catching up with the parents of another former student – a young man who’s now in college. He’d started with me back at the beginning of the pandemic, first in a small-group current events class, then in a U.S. History class on Outschool. I’d never met his parents in person. We’d only ever existed to each other as names on a screen, voices in a Zoom room, a signature on an email.
His mom thanked me. Specifically, she thanked me for how I taught U.S. History—not from a textbook, but from Jill Lepore’s These Truths, a dense, unflinching book that doesn’t shy away from the harder parts of the American story: the gaps between our founding ideals and our actual history, the fragility of democratic institutions, the economic fault lines that keep reappearing across two and a half centuries. Reading it wasn’t just a history class. It was a class in how to read something hard, sit with complexity, and think critically about a text that refuses to hand you a clean narrative.
She told me that the two of them had talked about the book together.
This is one of the things I don’t think people fully understand about teaching homeschooled students online: I’m rarely just teaching a kid. Sometimes I’m teaching a family. Sometimes a parent is half-listening from the next room. Sometimes I watch a younger sibling arrive in my classroom two or three years after their older brother or sister graduated, already primed by dinner-table conversations about what to expect. Sometimes, like last night, I find out years later that a book we read together didn’t stay in the classroom.
I could not have known, six-plus years ago, at the panicked start of the pandemic, that what I was cobbling together as some Zoom links, a syllabus, a lot of improvisation would become what it is today. A business. A body of work. A way of teaching that families choose on purpose, often because they’ve heard from another family first.
Tomorrow, a new group of students logs on for the first time. Some of them I already know; returning students, siblings of former students. Others I’m meeting for the first time. I don’t know yet which of them will, six years from now, be sitting at a graduation party telling me what stuck.
But I know this: I am the luckiest teacher in the world. Not because the work is easy, but because I get to do work that matters, with students who are genuinely thinking, in a way that follows them home.
Here’s to year seven.
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