I was going the wrong way. Any New Yorker could tell you what the right way across the George Washington Bridge is—that’d be west to east, the direction that leads to, not out of, the city. But then, by dint of this voyage, I was surrendering my right to call myself a NewYorker. I’d moved to town on Veterans Day, 1980, arriving at Penn Station with a sleeping bag, a backpack of clothes, and an Autoharp, in hopes of seeking my shining fortune there in the land of dreams.

Now, after five years of failing to become famous, I was leaving town with my tail between my legs, driving a U-Haul toward Baltimore—a city I’d come to love in time, but which no one, at least at the time, could have mistaken for a land of dreams.

The story of arriving wide-eyed in New York, of course, is one told so often that it’s hard to do it justice without falling into hilarious, creaking clichés. A story less frequently told, though, is the story of someone leaving the city thinking of herself as a miserable failure, not least because it’s the successes that transform into legends.

I didn’t have a legend in August 1985 when I slunk out of town by way of the GW Bridge. Mostly what I had was a big pile of dreams that had, with an almost operatic sense of disaster, failed to come true. In my own humble way, I thought of the wreckage of my aspirations at the time as my own personal Hindenberg.

Which is why returning to the old neighborhood this fall, after 30 years, as Barnard’s inaugural Anna Quindlen Writer-in-Residence, feels both exhilarating and more than a little strange. In 1980, I lived on the corner of 108th Street and Amsterdam, one flight above what might genteelly be referred to as an S&M dungeon; now, in 2014, I find myself settling into an apartment on West End Avenue and 106th, two blocks away, one flight above a nice young couple and their doe-eyed kindergartener.

The neighborhood has changed, to say the least. The S&M dungeon is now a grocery.The fake health-food store that used to sell drugs (marijuana came
in a small brown packet marked with an ink stamp that said “HEARTBEAT”) is now a bank. Everything’s shinier and more upscale on this part of the Upper West Side. It’s safer, to be sure, but the neighborhood has also lost some of its not wholly un-charming 1980s grunge.

But then, I’ve lost some of my own grunge as well. In 1980 I was a scared, if entertaining, young man carrying around the curious secret of gender dysphoria, a truth I dared not reveal to another living soul (except to an absolutely clueless psychologist up on 122nd Street). Now, 34 years later, I return to the old neighborhood as professor of English, a middle-aged woman, the author, among other things, of two college-age sons.

By almost any measure I am a happier and more serene individual than I was when I last lived in this neighborhood, and I thank my lucky stars that I live in an era in which this transition was possible. But it’s hard, as I walk up Broadway from my new home on 106th and West End to my office in Barnard Hall, not to remember the person that I was, and the partially vanished city in which he lived.

My roommate in those days was a young filmmaker just out of NYU named Charlie Kaufman.Years later he’d win an Oscar, and he’d become famous as
the creator of Being John Malkovich, Adaptation, Eternal Sunshine of the Spotless Mind, and Synecdoche, New York. Back then, though, he and I were just a couple of goofballs.

Barnard College, and Columbia University, loomed a few blocks north of our apartment, but we had almost no interaction with its world, which felt walled off and inaccessible. I remember one time trying in vain to gain access to the Columbia University library, which the psychiatrist I was seeing encouraged me to visit in order to learn more about transsexuality. A guard at the entrance told me I couldn’t go in, since of course I was not a Columbia student.

That library felt like a symbol of everything to me back then as a young, yearning artist—that there was a whole world waiting for me somewhere, if only I could learn to elude its gatekeepers. I was like young Charles Ryder, who laments in Brideshead Revisted: “But I was in search of love in those days, and I went full of curiosity and the faint, unrecognized apprehension that here, at last, I should find that low door in the wall, which others, I knew, had found before me, which opened on an enclosed and enchanted garden, which was somewhere, not overlooked by any window, in the heart of that grey city.”

One Saturday in December 1980, I ducked out of a sudden snowstorm into the dark caverns of the Cathedral of St. John the Divine. John Lennon had been killed the week before, less than a month after Reagan had been elected, and there was a biting melancholy in my heart that day, as if it was not clear whether the world I had arrived in was the one in which I wanted to dwell. I sat there in a lachrymose trance until an organist at the cathedral unexpectedly began practicing for the following day’s service. There, in that beautiful space, I heard the melody, performed in a set of variations for pipe organ, of John Lennon’s Imagine.

When the piece was over, I walked back out onto Amsterdam, my heart strangely light and open. In the interim, snow had transformed the city into something crystalline and unrecognizable—a place out of Dickens, or maybe Tolkien. As I stood there on the steps of the cathedral, I felt that things I had thought were impossible could in fact become real; that I would learn, in time, how to tell my story; that I would find the courage to come out as trans and begin to live an authentic life; that I would some day find, like Charles Ryder, the low door in the wall of the city that would open into that enclosed and enchanted garden.

The path across the George Washington Bridge, which I traveled five years later turned out, in fact, to be part of a much longer road, one that would lead, in its own curious way, back to where I had begun. After Baltimore, it took me to Colby College in Maine, where I spent 25 years as a member of the English department, where I would have a family, and get married, and publish my work, and yes, even find the courage—with the support of my family and students and my colleagues—to come out as trans and live the life that I had dreamed of in Morningside Heights all those years before. It would even lead me back, thanks to the vision of Barnard President Debora Spar and the welcoming grace of the College’s English department, to Morningside Heights, where I now self-consciously begin an appointment as an endowed chair named after one of my favorite writers in the world, Anna Quindlen, a woman who once wrote, “It turned out that when my younger self thought of taking wing, she wanted only to let her spirit soar.”

These days, as I walk around my old neighborhood, it’s tempting to look for signs of the person I once was. But people who look to the world and see only the ghosts of their own pasts are people who are blind to the present. It’s true that I could tell you a story about every street corner in Barnard’s neighborhood, a story in which the protagonist is a raggedy young man trying to find his courage—those are good stories, and given my adorable narcissism, I know I’ll visit them again. But there are a lot of other stories, quite frankly, that are more interesting.Young people still arrive in this neighborhood every day, in search of their shining fortunes. Many of them will go to Barnard. It’s my job now to help them, not by telling my own tales, but by helping them to find the courage to tell their own.

That low door in the wall—through a process as mysterious now as the passage of time—unexpectedly creaked open for me at last. At Barnard, in the years ahead, I will try to hold it open for my students, so that they too can find, against all odds, that enclosed and enchanted garden that awaits them on the other side.

—by Jennifer Finney Boylan

—Photograph by Juliana Sohn