I moved to New York City 20 years ago this week. I was 24 years old, had no job, only enough money to survive for about two months, exactly one friend (my roommate Ned) and lofty dreams of being a magazine writer. We’d scored a furnished, 2-bedroom sublet on the 19th floor of a Lower East Side co-op with a 30-foot terrace and an unobstructed view of Midtown. Our rent was $1,200 per month, which was a steal even then. The sublet was illegal, though, so we had to live below the radar. We were never allowed to change the name on the door or the mailbox; for all the co-op knew, we were the nice Jewish relatives of the unit’s rightful owners. We were neither Jewish nor related.
I’d recently finished an internship at the Utne Reader, in Minneapolis, and moved to New York because of that apartment. The owner’s niece was one of my fellow interns at Utne, and she knew I’d been thinking of trying out New York, so she put us in touch. I told the publisher of Utne about my upcoming move and he offered to write a letter on my behalf to the publisher of the New Yorker, a personal friend of his, asking him to meet with me. This felt like my ticket. I didn’t know what would ultimately happen for me in New York, but at the very least I had a guaranteed meeting at the New Yorker. I was off and running.
I called that publisher’s office every other day for the next three weeks, leaving messages with his assistant each time. He never returned the calls.
I called that publisher’s office every other day for the next three weeks, leaving messages with his assistant each time. He never returned the calls. I eventually gave up, confused and a little angry, but mostly just hurt. I’d heard the big city was tough, but I didn’t expect someone to ignore the request of a personal friend. I truly was a Midwesterner.
My first paycheck in New York came from a bygone academic magazine called Lingua Franca, for a freelance fact-checking gig that lasted two weeks. I’d sent the managing editor my resume and sole published clip, a 400-word review of an art exhibition catalogue I’d written for the Utne Reader towards the end of my internship there. Like all of the magazines I targeted in my initial job search, I knew of Lingua Franca from my time at Utne, a bi-monthly digest that billed itself as “the best of the alternative press.” I would spend hours each week in the magazine’s library, perusing 3,000 obscure periodicals from around the world looking for exceptional journalism to republish in our pages.
I’d gone into that internship knowing of five or six “good” magazines, and came out knowing of dozens. It was good knowledge to have when the New Yorker didn’t return your calls. I spent my first two months in New York wandering around town with the same resume-clip combo that had landed me the fact-checking gig at Lingua Franca. I delivered them, by hand and in person, to editors at Bomb, Commonweal and a dozen others. I still remember the look on the face of Bomb’s managing editor when I arrived, unannounced, to hand her my resume. She seemed impressed, if also incredulous.
The job lasted 10 months. I can’t say I killed it at SAR, but I did my best. Not quite a year in, I was asked to resign, not for anything I’d done wrong, but the magazine was bleeding out and would die completely within a few months of my departure. When a business bubble bursts and a recession is starting, what is there to write about except office equipment fire sales and rampant unemployment among the young professional class? I was shaken, certainly, but not upset. I’d had my fill of open bars, ostentatious launch parties and 25-year-old CEOs whose egos, it would turn out, weren’t the only things about them that were massively inflated.
So there I was, 25, with one real job on my resume and a lot more competition than I’d faced a year prior.
So there I was, 25, with one real job on my resume and a lot more competition than I’d faced a year prior, when it seemed like startups across the city were throwing jobs out like candy. I couldn’t tell you how many positions I’d been offered by those very dot-coms I wrote about during my 10 months at SAR; by November 2000, almost none of them still existed.
Through SAR’s publisher, I made contact with another magazine based in L.A. called RES, which was more my speed than SAR. It covered digital culture, not business: art, film, design. For RES, I wrote articles, for 25 cents a word, about new digital filmmakers, contemporary artists and web designers. One of the latter, the late Hillman Curtis, would like one of my pieces so much that he hired me to ghostwrite his second book, Making the Invisible Visible. From what I hear, that book is still taught in web design programs across the country. He didn’t pay much for the project, but he became a good friend. Once he paid my $600 rent when I couldn’t afford it on my own.
Then 9/11 happened. My already precarious situation in New York got much, much worse. I was barely 26 and looking at another year of living below the poverty line. So I applied to grad school in the humanities. It might have made zero practical sense, but at least it would get me out of New York for a little while.
My grad program, at the University of Chicago, was just one year, but I stayed in that city for two years after largely because it was so cheap. I started teaching there, and maintained my freelance writing career with magazines in New York and California. I continued to live below the poverty line. My last apartment in Chicago was infested with cockroaches; I paid $300 per month for my room.
For health insurance and stability, I got a job waiting tables at a restaurant. It was the only way I could survive.
In 2005 I returned to New York, reconnected with as many former contacts as I could and wrote for any magazine that would have me. I wrote about DJs and nightlife for Paper, independent cinema for the Independent Film & Video Monthly, and another book, about digital filmmaking, with Hillman Curtis. I started reading film scripts for money too, and for health insurance and stability, I got a job waiting tables at a Danny Meyer-owned restaurant. It was the only way I could survive.
I tried to get a full-time editorial gig, but at 30 years old, with a graduate degree, two book credits, and numerous magazine credits but only one full-time job on my resume, I found myself, paradoxically, both over- and under-qualified for just about every job I applied for. A common response to my applications was, “We went with another applicant for the position, but we’d love to have you write for us.” And so my satellite continued its orbit.
At the end of 2005 I was hired to teach a magazine writing class at Hunter College, and then, courses in film history and analysis, which I’d studied in grad school. In the meanwhile, I continued to wait tables, write for magazines, and read film scripts; I even started to write essays and test questions for the ACT college entrance exam. From 2008 to 2010 I anchored a political blog sponsored by the fashion designer Kenneth Cole, a job that allowed me to cover that year’s Democratic and Republican National Conventions, and from 2009 to 2014 I taught cultural criticism at NYU’s School of Continuing and Professional Studies, where my students were often accomplished professionals many years older than me. I also found a way to combine my two passions — writing and competitive distance running — by writing for Runner’s World and other athletic magazines. Most years since 2008 I’ve had six or seven W-2s and 1099s; in 2003 I had none.
Along the way it dawned on me that I’d become, essentially, a business in and of myself, and that all of my employers — even Hunter College — were, in fact, clients. Just as any company has a variety of clients and projects, so did I. And the benefit, just as any diversified company knows, is that if I lost one gig, I always had others to fall back on. If I’d had one job and lost it, then I’d have no jobs.
One night at the restaurant where I worked, a fellow waiter and I commiserated over the difficulties of maintaining a creative career in New York. He was an actor and had been on Broadway more than once. He said to me, “The thing people don’t realize is that you don’t just make it here and then you’re set. You make it, and then you have to make it again, and again, and again.”
After many years that often felt like I was developing more of a juggling act than a career, my routine finally clicked into a rhythm.
I finally quit waiting tables in 2012, and in 2013 I was hired to edit reports at a business intelligence and political risk advisory in Midtown, a job I got not just for my writing and editing credentials, but also for my work as a teacher. The firm wanted someone who could work with both veteran and novice writers, some right out of college themselves. After many years that often felt like I was developing more of a juggling act than a career, my routine finally clicked into a rhythm. In that position I have edited, and in some cases ghostwritten for, veteran intelligence and business professionals as well as heads of state from around the world.
I’m still at Hunter as well, teaching journalism exclusively now. I’ve served on committees, written countless letters of recommendation and had the privilege of helping more than a thousand people become better writers themselves. Some have even gone on to write for the New York Times, among many other publications. In 2016, one of my former students reached out to me, not to ask for a recommendation, but to offer me a job. She had become an editor at Forbes, and they were looking to increase the website’s film coverage. I took the job, and now a woman I used to edit edits me. Nothing could be more gratifying.
It’s been 20 years since I left that internship at the Utne Reader and moved to New York with nothing but a nice letter from a former colleague to open some doors for me in the big city. It failed to open the one door it was meant to, but I managed to wedge my foot in some others anyway. If there’s a lesson in this, it’s simply that perseverance matters. A lot.
But a secondary lesson may be that in building any career, even hardships and failure have great value. I remember choosing journalism as a career because I wanted to keep learning and experiencing new things, to constantly evolve and find the stories in what I learned and experienced. I never prioritized making money as a way to have life experiences; I wanted experiences, including difficult ones, to define my life. Vacations weren’t enough for me. I wanted unpredictability, and that’s exactly what the last 20 years have brought for better and for worse. It seems to me that’s the whole point.
I’ve built a career I’m proud of. Best of all, I built it myself.
I may have never written for the New Yorker or even the New York Times, but I’ve built a career I’m proud of. Best of all, I built it myself.
One night several years ago, when I was still waiting tables, I had a long talk with an investment banker who’d quit his job to open a bar. We talked about the paths we’d both taken thus far, our respective struggles and concerns, and our hopes for where it would all lead us. He said something I’ll never forget, and has become a kind of mantra for me, one I’ve even shared with students. If you’ve stayed with me this long, I offer it to you as well:
“At the end of the day, whoever has the best story wins.”