Two Words that Changed a Life

In his freshman algebra class in Coal City, West Virginia, Caleb Miller’s teacher one day paused the usual work with equations and gave a different kind of homework assignment, this one with no single right answer:

“Imagine 10 years from now, what is your life going to look like?”

Miller wrote that, in a perfect world, his future self would have graduated from Harvard, gone on to medical school, and become an amazing doctor. But to hedge his bold aspirations, he added, “OBVIOUSLY, none of that is going to happen.”

His teacher returned the graded paper with one thing marked: the line about Harvard, circled in red, with two words beside it — “Why not?”

“It’s a simple thing, a small thing, but I had never taken that question seriously up to that point. Growing up in West Virginia, you don’t see education as a path out,” says Miller, whose great-grandfather, grandfather, and father all worked in the coal mines. “It was the first time I had a teacher tell me that I had permission to take this crazy dream seriously.”

Fast forward to today. Miller did end up graduating from Harvard College in 2020 with a degree in mathematics. Soon, he will add a master’s from the Harvard Graduate School of Education, where he completed a yearlong teaching residency at nearby Somerville High School. While still interviewing for full-time positions for after he graduates, he hopes (and suspects) that 25 years from now he will still be teaching high school math.

“I am one of the people who credits a good teacher with a radical change in life trajectory,” says Miller. “Now, as a teacher myself, and thinking about all the million tiny things you do every day, I can’t imagine Mr. Perkins thought his comment would be this golden ticket. But it really had a profound effect on me. Maybe, 10 years from now, a student will look back on something we did in class, and it will matter to them. That possibility makes the work feel worth doing.”

It was a circuitous path to teaching for Miller, and for that, he’s grateful. Drawn to the prestige and paycheck of a career in finance, he first moved to Chicago after Harvard College to work as a quantitative trader. He was, in short, miserable.

One day, an executive spoke to the new hires and shared what he called the happiest time in his life: trading marbles in elementary school until he had more than anyone else. Miller thought the story was a little wild. But it got him thinking about when he’d been happiest at work — as an undergraduate, serving as a course assistant for math classes.

Now in HGSE’s Teaching and Teacher Leadership (TTL) Program, Miller teaches three sections of geometry five days a week before hopping on the Red Line to get to his own classes. Often, he’s correcting student homework while completing his own. Though his roommate (a TTL graduate) and program leads warned him that the pace can be challenging, he can think of no better way to prepare a teacher.

“Teaching is one of those embodied jobs where you have to be immersed in it. You have to get reps doing the actual thing, and I struggle to imagine a different setup,” says Miller. “It feels like it is hard because it has to be.”

Miller says he’s especially grateful to the donors who generously supported his financial aid, both at Harvard College and the Ed School, making a career in teaching feasible in the first place. At HGSE, Miller received the Harvard Fellowship for Teaching, which helps qualified students pursue a career in the classroom. 

He says he values being in a community with kind, smart, and thoughtful people who care deeply about teaching and are driven to get better. “The breadth and depth of my classmates is amazing,” says Miller. “I have learned so much from them, and I know they are going to leave here and do amazing things.”

Earlier this year, Luisa Sparrow, Ed.M.'14, the 2025 Massachusetts Teacher of the Year, spoke at a TTL student event. She compared teaching to a gas: it expands to fill whatever space you give it. “Given the rate of burnout, especially for new teachers, I think about this a lot as I try to strike a balance between my different responsibilities,” Miller says. 

There are little wins along the way. He mentions a freshman in his geometry class who started the year as a non-honors student, moved up to honors, and is now earning straight A’s. The boy’s mother texted him to say this is the first time her son ever felt confident in his math ability.

Yet, there are days when the weight of students’ lives makes geometry feel almost beside the point. “I recognize it can be hard to ask students to label a right triangle when all of this stuff is going on in the world,” says Miller. 

On two occasions this year, his students saw ICE agents detain people outside of school before the day began. But he also believes math class can be a reassuring place, even briefly, because students have control over the outcome. And maybe, in that space, they begin to see that focusing on their education can put them in a position to change the things they do not like happening around them.

“Getting to know someone over the course of a year and watching how they change and grow and see that they did better today than yesterday because of something you said to them keeps you going,” says Miller. “With this job, I’m still beating my head against the wall sometimes, and I still lose sleep. But it feels worth it in a way I never really felt before.”