Ever since entering the world of “elite” independent schools as a working-class kid, I have wrestled with feelings and questions of belonging.

Fish Out of Water

My first days as a full-ride scholarship student at a New England boarding school were marked by the discomfiting reality of knowing beyond the intellect, deep in my core, that I didn’t belong. My new classmates spoke differently, dressed differently, joked differently, and carried themselves with a sense of ease and self-confidence that bore little resemblance to my own working-class way of being in the world. 

I experienced directly and for the first time the lives of the exceptionally wealthy, and despite some resemblance by way of complexion, we were like different species. I’d seen these people from afar: on television, in movies, and in the homes that my mother sometimes cleaned for extra cash, but engaging with them in their natural habitat was different.

In one of my first exchanges with my new classmates, my truly impressively loud Burrrp!, which would have delighted my less sophisticated public school friends, was met with embarrassed-for-me silence. Their parents had jobs involving numbers, buying or selling, or something else that felt similarly abstract, while my mother worked as a home health aide and cleaned houses and my stepfather delivered mail. If their parents had served in the military, it was in leadership, while my father, a high school dropout, was forced onto a patrol boat during the Vietnam War, living through scenes reminiscent of Apocalypse Now

Beyond that, my classmates had study skills and tutors, while the skills, intellect, and cultural savvy that had brought me success in my former public school — a school with a roughly 75% of graduation rate — were simply not enough to buoy me. And while this student body was considerably more racially diverse than the one I had left behind, I largely experienced my classmates as a singularity: a group clearly united by assumptions, norms, and values, as a globe-spanning class.  

I remember clearly my history teacher, a local Episcopal priest, rightly chiding our class for whining about grades, noting, “So this is what it sounds like when the upper middle class gets cranky!” After class I sheepishly but with a burgeoning inner resolve made it clear to the teacher that I was not, in fact, upper middle class. My response signaled an important shift in my life: I had developed a firm awareness of my class and the class of those around me.

My poor grades and occasional troublemaking led to my being asked to leave at the end of the year. I petitioned and they accepted my plea, offering me a spot in the sophomore class at full tuition. While their decision to ask me to leave was entirely reasonable, this “offer,” for a scholarship student, wasn’t. It was back to public school for me, yet the experience had left an indelible mark and set me on a path I never would have predicted at the time.

Can You Go Home Again?

Ten years later, I returned to this school as an intern in the school’s academic support program in a quest to find and save versions of my younger self — a decision that has now grown into what is nearing a twenty-year career in education. Upon my arrival, I was enthusiastic to share with this community the ways I’d grown and changed, the struggles I’d faced, and my determination to be an advocate for students on the margins. 

After reminding my former math teacher who I was (in the span of ten years, she’d forgotten), she pointedly asked, “What are you doing here?” I felt as if I’d failed one of her tests again.  Unlike my 14-year-old self, however, 24-year-old me had enough confidence and wisdom to politely smile and change the conversation. 

It wasn’t until then, however, that I realized the degree to which adult complicity or perhaps ignorance had played a role in my ninth-grade experience. It wasn’t just about the kids and it wasn’t just about class. It was about a culture that was unconscious of itself – like a machine humming silently in the background that our minds tune out over time, that only when we stop and focus, assaults us with its conspicuousness. 

If I had replied, I might have told her about the time a student told me, “You look like you’re homeless,” because of the green hand-me-down parka with a faux-fur hood I was wearing (long before they were cool), or about the rage that then led me to punch him in the face. Or about the time I thought I’d finally found a working-class friend with whom I could commiserate, only to visit his grand home and have my hopes dashed. I might have told her that my head was so clouded with fears and frustrations that Algebra ranked pretty low on my list of concerns. 

More likely, however, I would have invited her into a conversation about the purpose of our schools: who they’re for, what function they should serve, and what it might mean to better ensure that every student who receives an acceptance letter knows that they matter. I may have noted that under such conditions, I would have stood a better chance of success, but that in retrospect I also recognize that I possessed enough agency even at that age to have made better decisions to carve out a different future for myself. 

Rage into Empathy

I long ago relinquished the bitterness I held tightly within me, setting free the flame that burned within me so that it might fuel my commitment to being an advocate for our students who, in all likelihood, feel othered in ways my own position makes difficult to grasp. The tears that used to sometimes come when I imagined my young self — a child — full of the rage, sadness, and confusion of that year, have directed and redirected me toward a more expansive empathy. These feelings allow me to better navigate fundamental tensions at the heart of our work in independent schools — schools that I’ve grown to love for the deep sense of community they can foster, their love of rich intellectual life, the complex and beautiful students who inhabit them, and the promise they hold of becoming intentional microcosms of the world we want to create.