Middle Class, But Raised in an Upper Class World

by Emily May

I grew up in some of the most exclusive neighborhoods in the nation thanks to my dad’s position as a prep school teacher and coach.

My brother, sister and I rode our bikes up and down hallways carpeted with Saarinen rugs, and spent our summers on a prep school campus that educated the bluest of blue bloods, including several U.S. presidents, prominent businessmen and authors. We settled for a few years on Long Island, where my dad was a teacher and my mom was a school librarian at the exclusive day school we attended, and my siblings and I were granted a ticket into an elite world that was far from our birthright.

My friends’ houses were palatial — equipped with swimming pools, trampolines, untouched marble kitchens and a view. My former schoolmates routinely turn up in the society pages of the Sunday Times. My family lived in rented houses, and my sister and I shared a room. My mother recently disclosed that my father’s income could not cover the rent of our three-bedroom duplex. I was oblivious to any financial stress at the time; we had a big front yard and woods in the back, and for the most part, we were happy.

My friends’ eighth birthdays were celebrated with a limo into the city for tea at the Plaza for four and a stop into Tiffany’s. On Saturdays, we would go to the stable and ride horses, and summer weekends were spent in the Hamptons. For our birthdays, my mom would invite our friends over, and we would have a water balloon fight, or scavenger hunt. Our friends’ moms were always amazed at my own mom’s creativity. My best childhood friend (whose dad put us up at the Essex House and took us to a Broadway play and Windows on the World when we were 11) lived in a mansion on the bay with both of her parents who were enduring a years-long, bitter divorce, and had reached a legal stalemate over the house. There was an unarticulated heartbreak in my friend that I couldn’t identify until much later — one that I’d never felt living in the small house where my family ate dinner together every night.

I remember spending a weekend at another friend’s house: She had a princess canopy bed, every Disney movie ever made, and an entire basement full of the latest dolls, toys and games on the market.

“Let’s play outside,” she said. “There’s nothing to do in here.” We spent the afternoon on her tire swing.

But my friends weren’t snobby, and never looked down on me for the obvious wealth disparagement that might have divided us. I had noticed that my family had one minivan and my friends’ moms all drove BMWs, but I never thought to care and my friends never seemed to either.

Before I entered high school, my father took a teaching job at a boarding prep school, and his three children were funneled through. My classmates were the sons and daughters of CEOs, Wall Street titans and Donald Trump. There were more weekends at beach houses and Manhattan, and lunch at the Yale Club. I was fully aware that I wasn’t part of that world, that my pass was though a back door, but as all teenagers do, I wanted to be like my friends. I was swept up in a wave of materialism that took me until college to acknowledge as a treadmill of vacuousness, a dead end — there’s always more to have. If all high schools lend themselves as laboratories for studies in material culture, perhaps none are so fine-tuned as prep schools, where the students’ sense of taste and class are so keen that the stitch of a hem or the heel of a shoe betrays a desirable or undesirable brand, and the wearer is ranked accordingly.

But even before college, material wealth was revealing itself as a dubious path to contentment.

One weekend during our junior year, I was at the mall with two friends, Sarah and Michelle. Sarah had just placed a generous order through that season’s J. Crew catalog with her father’s credit card (I’d been poring over the same catalog for weeks, revising my wish list and adding up the grand total countless times. With each tally, the list grew a little shorter as the reality of my babysitting money sank in).

While Michelle was looking at jewelry in Nordstrom, Sarah muttered to me, “I wish I had Michelle’s money. She can buy whatever she wants.” I was dumbfounded, sad and on a more instinctual level, disgusted.

I’m grateful for my parents’ emphasis on our education. I was taught by first-rate instructors who unfailingly treated their profession and students as more than a job; our edification was their calling and life’s work. I’m most grateful for the fact that despite our family’s proximity to exorbitant wealth, my parents were never impressed by money. But having been raised in that world, I battle between my own aversion to money and affinity for nice things and beautiful homes. I feel I deserve vacations and luxury brand make-up and haircuts that are ludicrous purchases on my income. I feel strangely at home in a leather-interiored Audi while I can intellectually criticize that same indulgence of luxury.

My sister and I share an almost ingrained distaste for tackiness — let’s be honest, classlessness — our cultivated snobbishness having no basis in our tax brackets. But we also learned to distrust the rich’s idle obsession with that very specific armory of possessions: Ivy MBAs and Chelsea and Anguilla and rehab and Z4s and the list never ends.

Perhaps this is where some confusion begins: If we were economically middle class raised in an upper class world, where do we belong? But if I’ve truly learned anything from my expensive education, it’s that concerns such as those regarding my own or anyone else’s “class” are not the vital questions that demand lengthy consideration, and that education itself is real enough wealth.

After graduating from college into such a vicious job market, of course I dream of a trust fund I never knew I had, just waiting to be revealed to me (maybe on my 30th birthday?). But more than that, I’m grateful for having an outsider’s glimpse into the world of the monied, if only to cross wealth off the list of things that I think will satisfy me. I thought of Sarah when a friend recently relayed advice from her mother, a Lebanese-born immigrant to the United States: “Some people are so poor they only have money.”

Previously: Growing Up with Rich Kids Made Me Feel Rich, Too

Emily May makes art and talks about books.

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