Confessions of an Outsider in Elite Black America

As a scholarship student at a fancy private school, I gained entry to a world few Americans see: rich, privileged and black. I decided I wanted no part of it.

Confessions of an Outsider in Elite Black America

My cousin swept onstage in a cloud of white, not so much walking as floating. She was resplendent in a gown of white satin, starched petticoats, hips gently swaying. Her Rubenesque form overshadowed the slender darkness of her escort, elegant in his tux and tails. The announcer read her name as she glided forward. Her escort, son of Dr. and Mrs. Someone-or-other, moved toward her in a coordinated dance, extending his arm in a way that made her seem like an extension of him. Her skirt belled out as she dipped into a perfectly executed curtsy that no doubt took months to perfect.

She looks like a dinner napkin. My inner critic snorted. I began a one-woman tirade, railing against and mocking the cotillion, its participants, and the “talented tenth” mentality it espoused. The swirling skirts, sweeping waltzes, and rhythmic stepping of one of black society’s oldest traditions had reduced me from a confident 30-year-old to a sniveling teenager in mere seconds. I was jealous of my cousin, a girl nearly half my age, because she had managed to infiltrate that elite echelon I had always seemed to orbit around yet would never truly be a part of. The feeling took me back to my teenage years, which I spent with my face pressed against the glass of elite black society.

My mother was likely the reason I never quite learned “my place.” I grew up in East Cleveland, a majority black community where white flight, exploitative public policy, and the crack epidemic had all taken their toll. By the time I started kindergarten, the city was in a state of fiscal emergency. Growing up on welfare in a downward-trending neighborhood came with certain accompanying societal expectations. My mother shattered every single one.

We were poor, but she never allowed it to define us. We didn’t use slang at home, but I did learn rudimentary French. We had food stamps (the actual paper kind), but we didn’t eat “struggle meals.” Instead of fast food, sloppy joe mix, or overprocessed boxed meal “helpers,” dinner consisted of delicacies like coq au vin, chicken piccata, and stuffed acorn squash. Instead of watching television, we played Scrabble or chess. Instead of Goodnight Moon, my bedtime stories were by Tolkien and Shakespeare. Learning was revered for its own sake. “Knowledge, what’s in your head, it’s the only thing you own,” my mother often said.

High test scores and a quirk of fate gained me a benefactress, a woman who personally provided me with a full-ride scholarship to one of the most prestigious private schools in the country: Hawken. I went from an elementary school with 800 students, 99 percent of them black, to a middle school with just over 200 students, 14 of which were black. I went from being the smartest kid in class to being academically adequate. I was far less worldly than any of my peers. To call it culture shock would be an understatement.

Until I set foot on the verdant, rolling lawns of Hawken’s middle school campus, I’d had no real understanding of what it meant to be poor. In East Cleveland, my quality of life had been different from that of my classmates not because we’d had more resources than the next person, but because of how my mother chose to make creative use of those resources. At this new school, I was simply out of my league.

I knew I lived in the hood, but I didn’t understand how negatively my neighborhood was perceived until I went to Hawken. Like all cities, East Cleveland had a nicer, historic side and a ’round the way side. I lived ’round the way, down the hill, where people were afraid to go. My school bus wouldn’t even pick me up from my house. Instead, I had to walk nearly a mile up the hill to be picked up at a classmate’s house.

That classmate was the grandson of one of the founding families of the Cleveland chapter of Jack and Jill, a private social club for children of the black elite. Black or white, these children all had a pedigree. I was on a scholarship. My mother was on welfare. Even among minorities, I was a minority.

Don’t get me wrong, there was a strong sense of solidarity among the handful of black and brown students. We all sat together on the back of the bus. Most of the black boys and a couple of the white ones spent the hour-long ride freestyle rapping and providing beats for each other. The son of a prominent family that ran a funeral home once created a rap that went like this:

From the streets of EC so I stay on my grind — but I’m headed up to Hawken and I’m bout to get mine. Yeah, I rep my hood cause the ghetto what made me, you can hate while I give this ghetto dick to your lady.

He knew nothing of the ghetto. His family home, while technically in East Cleveland, was nestled safely in the historic district, far from the broken street lamps and corner dope boys he rapped about and that I knew by name.

I didn’t like how he used his zip code to lay claim to a lifestyle he knew nothing about, to glamorize a life I was desperate to escape, but I didn’t call him out on it. He knew more about “thug life” than any of the white boys on the bus with us, and black folks had to stick together, whether we liked it or not. There were simply too few of us for it to have been otherwise.

The unwritten rules of blackness that I’d learned in elementary school no longer applied in this environment, but there were new rules to learn, rules for exceptional black folks to help each other navigate a dangerous white world.

Some of these rules were no-brainers, like never snitch on another black student, never make fun of another black student’s complexion or call them “ashy” in front of white people, whether you like them or not, always make room at your lunch table for another black student, and of course, if you are in a room full of white people and the N-word is used, you are morally obligated to fight.

In seventh grade, Hawken students spent a week away from their parents on an experiential learning adventure. After six weeks of selling candy bars and collecting pennies door to door, I was able to afford the cheapest of the eight trips my school offered. I ended up camping in the hills of West Virginia. I was one of just three black students on the trip.

After a particularly difficult and rainy day of hiking and climbing, we piled into a van and rode 40 miles to the closest town. Stinking and chilled to the bone, the nine of us took turns huddling against the fireplace grate at a local restaurant. An old lady who looked like Red Riding Hood’s grandmother introduced herself as the owner and cook. She served us giant New York–style pizzas, the first meal we’d eaten in days that wasn’t cold or cooked over an open flame.

One of my black classmates was known to be rude and messy. After dinner, he stood near the fireplace grate to dry his dripping wet pants. He hadn’t gotten the tough, water-resistant pants and wicking socks our packing list recommended, so he was soaked to the skin. He must have gotten too close to the grate, because his pants began to melt and smoke.

I will always associate the scent of burning plastic with his tear-stained face. As the cook and our wilderness guide poured water on him to extinguish his pants, the other boys laughed and called him “a big, stupid ape.”

My friend, a fellow black classmate, raised her voice and shouted: “You do not get to call him a monkey! You do not get to do that!” Our white classmates dipped their heads, chastened. The rude boy looked at us and smiled. We smiled back.

We hated that boy. He was mean, a bully. He cussed too much and said crass things about female body parts. His breath smelled and he was always sweating, but in that moment, none of it mattered. He was ours and we would not fail him, or leave him standing alone while the white kids mocked him for being fat and black.

For the most part, the black elite I grew up rubbing elbows with were a lot like me. None of them were uber-rich in comparison to our white classmates. One or both of their parents had jobs, none of them had been raised by nannies. The few families that did have housekeepers or other support staff didn’t have live-ins, their homes were spacious but didn’t have private “wings” where their parents entertained. My black peers, for the most part, lived middle-class lives. It wasn’t income that made them part of the black elite, but a generational pride and a sense of obligation that came along with being part of “the talented tenth.”

Coined in 1903 by black scholar W.E.B. Du Bois, the talented tenth concept was the idea that 10 percent of African-Americans had the opportunity for upward mobility through higher education, and that this 10 percent were morally obligated to be the “rising tide” that lifted the black population out of their intended status as permanent second-class citizens. In other words, due to structural disadvantages in society, black people did not have the same access to opportunities as their white peers, so the few of us who did would have to take advantage of those opportunities and lift up the rest.

The common refrain “you’re not really black” was an insult at home, but at school it was a compliment, a way of saying I had learned the game and played it so well that white people no longer perceived my skin color as a handicap. I understood that my potential for success depended largely on my ability to navigate and thrive within a white, upper-class world.

My white classmates whose parents and grandparents had attended Ivy League institutions often told me I was lucky that I would get affirmative action and didn’t have to worry about getting into a good school. Never mind the fact that I could barely afford the college application fees. I was visibly black but didn’t act like a stereotype, therefore they assumed I would be handed opportunities white students had to work hard for.

The black students at my school all fed into the talented tenth narrative. When someone said we “didn’t act like other black folks,” instead of reminding them that blackness is not a monolith and that there is no set way to act black, we said “thank you.” We thought we were special, and therefore, deserving.

We all competed with each other for musical and vocal solos, parts in the school play, and leadership and networking opportunities. We learned to be as cunning as jackals, often stealing opportunities right from under our fellow black peers. I once landed one of two highly coveted student seats on a diversity and inclusion board by casually pointing out to the chairman that my closest competitor was so light-skinned, she would barely look black in pictures. My visible brownness would provide the “token diversity” needed for the glossy photos that would go out in the school’s quarterly report.

We were all outsiders, desperate to be the one exception that white society let in, never understanding our own power.

But no matter what I did, I never had a shot at being accepted into elite black society. None of my classmates would come to my house, regardless of their race. Many black parents celebrated my accomplishments and were kind and generous to me, but they wouldn’t have approved of me dating their sons. I didn’t have the pedigree.

I was reminded of my inferior status every spring, when most of the black students and all of the black girls (but me) had cotillion rehearsal. I wasn’t an envious child, but I did envy the debs in their beautiful white dresses and their escorts in tuxes with tails. Because my mother didn’t pledge the Alpha Kappa Alpha sorority at a historically black college, I couldn’t leverage family friendships to build inroads with the black elite like my cousin had. My mother probably would have found a way for me to participate in cotillion if I had asked, but I was too embarrassed to do so. Selling candy bars at the mall to finance a school trip was one thing, but to wear a pretty dress, walk on the arm of an eligible young man, and “come out” as part of a society I would never truly be accepted in felt like a waste of time and energy.

I pretended to hate cotillion. I told my mom that the tradition was archaic and elitist, that you couldn’t pay me to go, that I was glad not to have to attend all those long, boring rehearsals. I never let on how much I wanted to be part of that glittering throng, how strongly I desired to be on the inside.

Eighteen years later, I’ve stopped feeling sorry for myself. Living on the fringes of elite society bought me a golden ticket into predominantly white spaces, but my socioeconomic status ensured that it would never become a backstage pass. I could successfully infiltrate elite spaces, but I would never thrive in them. Eventually I dropped out of college. I worked retail and other dead-end jobs before becoming a community organizer. I gave up a political career to start my own business making small-batch hair and skincare products. Last fall, I realized that although I was eking out a living, deep down I was miserable. By October my company had failed spectacularly, and I had no idea what I was going to do for a living.

The only time I was truly happy was when I was writing, and although I knew I had talent, it had also been drilled into me that writing wasn’t a career. What I had learned from my experience in elite society was that as a black woman I wasn’t free to take risks that might not pay off. But I decided to take the leap anyway. Becoming a writer has been an act of liberation because I am freeing myself to do what I love. I have chosen to live life on my own terms instead of by the unwritten rules society has designated for me. By abandoning my pointless quest to become an insider, I have become what I always wanted to be: myself.