There were about nineteen hundred kids at Whitney Young, and from my point of view they appeared universally older and more confident than I’d ever be, in full command of every brain cell, powered by every multiple-choice question they’d nailed on the citywide standardized test. Looking around, I felt small. I’d been one of the older kids at Bryn Mawr and was now among the youngest of the high schoolers. Getting off the bus, I’d noticed that along with their book bags a lot of the girls carried actual purses.
My worries about high school, if they were to be cataloged, could mostly be filed under one general heading: Am I good enough? It was a question that dogged me through my first month, even as I began to settle in, even as I got used to the predawn wake-ups and navigating between buildings for class. Whitney Young was subdivided into five “houses,” each one serving as a home base for its members and meant to add intimacy to the big-school experience. I was in the Gold House, led by an assistant principal named Mr. Smith, who happened to live a few doors down from my family on Euclid Avenue. I’d been doing odd jobs for Mr. Smith and his family for years, having been hired to do everything from babysitting his kids and giving them piano lessons to attempting to train their untrainable puppy. Seeing Mr. Smith at school was a mild comfort, a bridge between Whitney Young and my neighborhood, but it did little to offset my anxiety.
Just a few kids from my neighborhood had come to Whitney Young. My neighbor and friend Terri Johnson had gotten in, and so had my classmate Chiaka, whom I’d known and been in friendly competition with since kindergarten, as well as one or two boys. Some of us rode the bus together in the mornings and back home at the end of the day, but at school we were scattered between houses, mostly on our own. I was also operating, for the first time ever, without the tacit protection of my older brother. Craig, in his ambling and smiley way, had conveniently broken every trail for me. At Bryn Mawr, he’d softened up the teachers with his sweetness and earned a certain cool-kid respect on the playground. He’d created sunshine that I could then just step into. I had always, pretty much everywhere I’d gone, been known as Craig Robinson’s little sister.
Now, though, I was just Michelle Robinson, with no Craig attached. At Whitney Young, I had to work to ground myself. My initial strategy involved keeping quiet and trying to observe my new classmates. Who were these kids anyway? All I knew was that they were smart. Demonstrably smart. Selectively smart. The smartest kids in the city, apparently. But wasn’t I as well? Hadn’t all of us—me and Terri and Chiaka—landed here because we were smart like them?
The truth is I didn’t know. I had no idea whether we were smart like them.
I knew only that we were the best students coming out of what was thought to be a middling, mostly black school in a middling, mostly black neighborhood. But what if that wasn’t enough? What if, after all this fuss, we were just the best of the worst?
This was the doubt that sat in my mind through student orientation, through my first sessions of high school biology and English, through my somewhat fumbling get-to-know-you conversations in the cafeteria with new friends. Not enough. Not enough. It was doubt about where I came from and what I’d believed about myself until now. It was like a malignant cell that threatened to divide and divide again, unless I could find some way to stop it.
* * *
Chicago, I was learning, was a much bigger city than I’d ever imagined it to be. This was a revelation formed in part over the three hours I now logged daily on the bus, boarding at Seventy-Fifth Street and chuffing through a maze of local stops, often forced to stand because it was too crowded to find a seat.
Through the window, I got a long slow view of the South Side in what felt like its entirety, its corner stores and barbecue joints still shuttered in the gray light of early morning, its basketball courts and paved playgrounds lying empty. We’d go north on Jeffery and then west on Sixty-Seventh Street, then north again, zagging and stopping every two blocks to collect more people. We crossed Jackson Park Highlands and Hyde Park, where the University of Chicago campus sat hidden behind a massive wrought-iron gate. After what felt like an eternity, we’d finally accelerate onto Lake Shore Drive, following the curve of Lake Michigan north toward downtown.
There’s no hurrying a bus ride, I can tell you. You get on and you endure. Every morning, I’d switch buses downtown at Michigan Avenue at the height of rush hour, catching a westbound ride along Van Buren Street, where the view at least got more interesting as we passed bank buildings with big gold doors and bellhops standing outside the fancy hotels. Through the window, I watched men and women in smart outfits—in suits and skirts and clicking heels—carrying their coffee to work with a bustle of self-importance. I didn’t yet know that people like this were called professionals. I hadn’t yet tracked the degrees they must have earned to gain access to the tall corporate castles lining Van Buren. But I did like how determined they looked.
Meanwhile, at school I was quietly collecting bits of data, trying to sort out my place inside the teenage intelligentsia. Until now, my experiences with kids from other neighborhoods had been limited to visits with various cousins and a few summers of city-run day camp at Rainbow Beach, where every camper still came from some part of the South Side and nobody was well-off. At Whitney Young, I met white kids who lived on the North Side—a part of Chicago that felt like the dark side of the moon, a place I’d never thought about nor had reason to go to. More intriguing was my early discovery that there was such a thing as an African American elite. Most of my new high school friends were black, but that didn’t necessarily translate, it turned out, to any sort of uniformity in our experience. A number of them had parents who were lawyers or doctors and seemed to know one another through an African American social club called Jack and Jill. They’d been on ski vacations and trips that required passports. They talked about things that were foreign to me, like summer internships and historically black colleges. One of my black classmates, a nerdy boy who was always kind to everyone, had parents who’d founded a big beauty-supply company and lived in one of the ritziest high-rises downtown.
This was my new world. It’s not to say that everyone at the school was rich or overly sophisticated, because that wasn’t the case. There were plenty of kids who came from neighborhoods just like mine, who struggled with far more than I ever would. But my first months at Whitney Young gave me a glimpse of something that had previously been invisible—the apparatus of privilege and connection, what seemed like a network of half-hidden ladders and guide ropes that lay suspended overhead, ready to connect some but not all of us to the sky.
* * *
My first round of grades at school turned out to be pretty good, and so did my second. Over the course of my freshman and sophomore years, I began to build the same kind of confidence I’d had at Bryn Mawr. With each little accomplishment, with every high school screwup I managed to avoid, my doubts slowly took leave. I liked most of my teachers. I wasn’t afraid to raise my hand in class. At Whitney Young, it was safe to be smart. The assumption was that everyone was working toward college, which meant that you never hid your intelligence for fear of someone saying you talked like a white girl.