Would You Send Your Child to Boarding School?

For me, a kid from West Virginia, boarding school was my best bet for the kind of education that kids from Greenwich or the Upper East Side take for granted. My mother, a Cassandra for income inequality in the 1980s, knew that attending a top college was my shot at getting into and staying in the middle class. She feared that the local options for high school wouldn’t provide the college prep courses and connected admissions counselors that grease the skids for college acceptance. And so off I went, with a trunk of hand-sewn clothes my mother and grandmother made from old Vogue patterns that they deemed “preppy.”

Of course, what one’s grandmother thinks will be in style with wealthy New England girls is obviously totally wrong. My plaid skirts and knee socks were out of place amongst my classmates’ Laura Ashley cotton dresses and Indian-print t-shirts. I called home and begged my mother for different clothes, which was totally out of the question, of course—we’d barely had the money to acquire the first wardrobe, much less a second. So I made do with what I had and struggled through the first year, out of place and lonely.

But despite that, in many respects it was a good experience. It was a community entirely different from my West Virginia small-town upbringing, and I soon became as comfortable on the Upper East Side as in Appalachia. (Or rather, I made peace with the fact that I was a weirdo and would never really fit in anywhere.)

Boarding school was a window into a rarefied world, almost like a four-year anthropological study—except the group that I was studying is the group that controls, say, 99 percent of the country’s assets and probably most of Congress. This is worth knowing about, even if you’re not a major player. My time there showed me what was possible, professionally, and it made me acutely aware of America’s class structure in a way that remaining in our small, homogeneous town never would have allowed. It’s made me more aware of privilege, both my own and others’.

And because kids are kids, even wealthy prep-school kids, I made friends who remain my dearest friends to this day. I did go to an excellent college on a full scholarship, which I may not have been prepared for or accepted to if I’d stayed home.

But for my own kids? NO WAY. My mother wanted me to change our circumstances, not unlike the families that sent their kids off to the new world in the hope of a better life. It was painful, but I accepted that the pain was worth it. All things being equal, though—meaning if there are educational opportunities as good as boarding schools, but close to home—my boys will stay home. Teenagers still need their parents. They need Mom’s daily guidance on matters large and small; they need Dad scanning their faces at school pick-up for clues to the trials and tribulations of the day. They need the kind of peaceful respite from the struggle of adolescence that a loving, non-judgmental home should provide.

They also still need to be taught practical skills—like housekeeping, cooking, and budgeting—that I never learned as a teenager, and that I imagine that other young people with more parental guidance did. (The Internet has filled in the gaps for me. For all you boarding-school alums: Dab things thing with Clorox wipes. Braising is fool-proof. The simplest budget is an Excel file.)

And for purely selfish reasons, I’m not willing to part with my kids four years earlier than I have to. My husband, who lived at home until graduate school, can’t fathom the idea of boarding school. (“We’d pay how much so they can have their heads skated over by a Kennedy?”)

And he’s suspicious of the moral caliber of private-school children. “I’m not sure I want them associating with people who have those values,” he says, as if all their classmates will be the children of various pension-looting tycoons and junk-bond salesman.

“No high school is asshole-free,” I counter. He shrugs.

What’s worrisome to us is that in this country, kids have to be wealthy or wealth-adjacent to get a good education, and we are not especially either. And that might mean some scrambling.

Well, there’s always homeschooling.