When I graduated from college in 1999, the economy wasn’t just humming — it was roaring. Yes, the tech industry was making a lot of the noise, but everything else seemed to be doing just fine, too. Certainly we had typical senior-year jitters (Should we take the LSAT? Sure, why not). And the stakes, of course, seemed incredibly high, as they always do when you’re 21 or 22. I spent a few afternoons in the career services office, thumbing through binders (yes, actual binders) full of printed-out job postings, but nothing seemed that appealing. At my school, a lot of the business majors had already accepted jobs at consulting firms and investment banks before spring semester had even begun, but those of us who had majored in English or art history or, fuck, even French weren’t worried. Tout sera bien.
Because that was how it felt: Everything would be fine. And everything was fine! Or fine, anyway, for a white woman in America with an Ivy League degree; it was harder, then, to clearly see or imagine the people for whom it might not be so fine. It was an optimistic time, because why wouldn’t it be? Bill Clinton was still president. Most of us did not have cell phones. Social media did not exist. Even though everyone older than us complained that New York wasn’t what it used to be, because Giuliani had come in and sanitized everything, it still seemed like the coolest place on Earth.
And almost everyone I knew moved to New York, including me and my boyfriend. I got there the Monday after graduation and moved into my new apartment on the Lower East Side with my friend Lisa, who’d been living across the hall for the last two years. We painted one wall in the living room red and bought a futon — the cover had stars on it — at the futon store across the street. I paid $850 a month for a bedroom that fit a full-size bed and a child-size armoire that I bought in the Kmart on Astor Place. It seemed like a fortune after my four years in Philadelphia, where my rent had last been $415 a month for a huge bedroom in a beautiful house two blocks from campus, but I knew that, for New York, it was decent.
Besides, the family upstairs was living in an apartment the same size with four children. We heard them bouncing balls and running above our heads; from below, smoke from the bar on the ground floor of the building wafted into our second-floor apartment. I was awakened every morning at 5:30 when a truck would come to make deliveries to the Domino’s Pizza next door, the boxes thwacking on the ground with a kind of authority that didn’t care that people upstairs were sleeping.
I had no job and almost no money. My parents had given me the security deposit on the apartment as a graduation present, but now I was on my own. I was entranced by the classifieds section of the New York Times, with its pages and pages of appeals for secretaries and programmers and architects and retail store managers. I didn’t really know what I wanted to do. I knew I liked to be around words, but I wasn’t sure what that meant in terms of actually making money. Maybe now was the time to try something new. Maybe I could close my eyes and point to something on the page and that would be my destiny.
That was how 1999 felt, like anything was possible.
I had also begun 1999 in New York. I had taken the train down from Boston, where I’d been with my family for winter break, and my friend Marc and I were staying for the week between Christmas and New Year’s in his brother’s empty apartment on Leroy Street in the West Village. Marc’s boyfriend David was a senior at Wesleyan, and he took the LIRR into the city from his parents’ house to see Marc. He joined us and my future roommate Lisa and her friend S. for New Year’s Eve. I was wearing my glasses and a vintage coat with a fur collar, and my bangs were short. We took the subway to Midtown, to a party in an apartment near Times Square, where S. and David disappeared for awhile, and then we took the train back downtown to the Lower East Side. I knew S. and David did heroin — it was big among David’s crowd at Wesleyan — but it didn’t seem like anything we needed to worry about. Eight and a half years later, at age 30, he would be dead.
Lisa knew about a show at a club on Ludlow Street that later became The Dark Room but at the time had no name, and so we went there, and David got up on stage with the crazy Russian band with the shirtless frontman who was slicing pillows open and throwing feathers everywhere. I had never heard of the band, Gogol Bordello, but they seemed intense and exciting in a way I thought my life should be. I made out with a guy named Brian who gave me his phone number and I thought, I will be fine in New York.
Lisa worked from home as a trend forecaster for a woman who had been profiled in The New Yorker. Her job was to scope out what was going to be cool, which mostly seemed to entail her walking around our neighborhood and noticing what people were wearing and writing up reports to send to her boss in LA. (For example: "Clowns!") She had a turquoise iBook and a flip phone. I had neither, but I had walked into an employment agency as soon as I’d gotten to the city. They gave me a typing test and sent me out on job interviews at publishing companies and ad agencies and magazines.
My cousin’s wife’s sister, who lived in Brooklyn and was a few years older than me, had also introduced me to a few of her friends, who worked at impossibly glamorous places like Time Out New York and GQ and a literary agency, and I met with them too. A couple people I knew from college had immediately gotten jobs at “dot-coms,” but I wasn’t sure that was what I wanted to do. I was sure that I needed money, soon, so when I got offered a job assisting two sales reps, A. and L., at a magazine, I took it. The salary was $25,000 a year. The first day, one of my new co-workers told me there was a reason they had been so eager for me to start right away; my predecessor had walked off the job in tears.
I was supposed to answer the phone, open their mail, keep their calendars and their contacts in Lotus Notes, make their lunch reservations and their spa appointments, do their expenses — which always included dozens of crumpled-up taxi receipts — and assemble media kits. Every week, when the magazine came out, I went through and put Post-Its on their clients' ads and then typed up a letter for them and sent the magazine over via messenger. I thought I was too good for the job and so I was not good at it. What had I been thinking, taking an assistant job in sales?
We moved offices and my bosses no longer had their own offices, they had cubicles, and sometimes I made personal calls that they could hear, and they told me not to make personal calls at work. One day L. asked me to get four tickets for an Elton John concert at Madison Square Garden, and even though the show sold out in minutes I got the tickets. I printed them out and brought them over to L. triumphantly, and she looked at them and said with disgust that the seats were behind the stage and what was I thinking, getting seats behind the stage, she couldn’t take clients to a show and sit behind the stage, and I started crying. Later I heard L. on the phone, saying she was going to have to use a ticket broker; A. called me and told me not to worry about it. They each wanted to be the favorite. Obviously, I was miserable.
The bigger problem was that I wasn’t making enough money. My check every two weeks was $714, directly deposited into the Chase bank account I’d opened on my first day of work. I wasn’t paying back my student loans yet, but rent and utilities, MetroCard, food, and the occasional movie or new shirt meant that every month my account dipped several hundred dollars into overdraft. Then I'd get a check and pay off the overdraft and the cycle would start all over again.
On weekends I started teaching SSAT classes — the exam that eighth-graders in New York take to get into specialized high schools, like Stuyvesant — for $20 an hour. It helped, but the work was inconsistent. I relied on the kindness of others in my life. My boyfriend lived with his aunt and uncle, a dentist who worked on Long Island, in a rent-stabilized penthouse apartment on lower Fifth Avenue. They had no children and they doted on us, ordering us dinner from Sammy's Noodle Shop or taking us to Knickerbocker for burgers, and always, on weekends, buying us breakfast at Joe Junior's, the long-closed diner on Sixth Avenue. His aunt would get half a grapefruit. They also had a house account at Jefferson Market, so sometimes we would walk over there and get a rotisserie chicken for dinner and charge it to them, and eat it drenched in sweet, sticky Peter Luger steak sauce. I had never been to Peter Luger, but my boyfriend's aunt and uncle kept a bottle of their steak sauce in the fridge. They made everything better; they reassured me that everything was going to be fine, after all. And then tragedy struck.
I was in a cab on Houston Street on a Saturday morning in July. I don’t remember where I was going, or coming from, or why I was in a cab in the first place, because I didn’t take a lot of cabs, but in any case the driver had the radio on and the newscaster said that JFK Jr.’s plane had been lost on the way to Martha’s Vineyard and he and his wife Carolyn and her sister Lauren were presumed dead. It seemed impossible. He was so young, just 38, and handsome, and he and Carolyn lived in an apartment on North Moore Street in Tribeca, and she was gorgeous and the most stylish. I knew I would never be them and yet they seemed like an idealized version of New York existence — rich, beautiful, famous, elegant, impossibly cool.
Today people would mourn a death like this on social media, but in 1999 people went to mourn in Tribeca. The sidewalk in front of the Kennedys’ apartment was filled for days with flowers and candles and pictures of them, and filled with people. People just staring and crying and not believing. A few days later, the bodies were found in the Atlantic Ocean.
When I mentioned to a younger friend that this was one of those “I remember where I was when I found out” deaths, she laughed, incredulous. “JFK Junior?” she said. It was hard for her to imagine how much we had cared.
Two and a half weeks after Kennedy's plane disappeared, Tina Brown held a party for 800 people on Liberty Island in New York Harbor for her new magazine, Talk. The guests ranged from Madonna to Henry Kissinger; everyone was already talking about the magazine’s first issue, which featured an interview with then-first lady Hillary Clinton, discussing her husband’s infidelity. Even then, the party was extravagant, a blowout tribute not just to Brown herself but to the idea of the importance and power of magazines. If they had lived, John-John and Carolyn almost definitely would have been in attendance.
Ten years later, the late New York Times media columnist David Carr would reflect, “Too bad nobody saw the sharks circling in the harbor. Rather than the culmination of a century of press power, the Talk party was the end of an era, a literal fin de siècle.”
One of my friends from college was working at a dot-com in “Silicon Alley,” which was what people had started calling the Flatiron District, and she told me they were hiring writers and did I want to apply? I did. I had only been an assistant at the magazine for just over three months, but it was long enough. The new job paid $38,000 a year — more than a 50% raise — and I would get stock options and bagels once a week. I told L. and A. I was leaving in two weeks and they didn’t seem surprised, mostly just irritated that they were going to have to find another assistant so soon. I felt bad, but not that bad.
I started my new job right after Labor Day. The office was on 22nd Street, between Sixth and Seventh avenues, and almost everyone was under 30. Thirteen years later, oddly enough, I would end up in another job, at another startup, just a block away. In 1999, I became good friends with the woman who sat next to me, who was 26 and married, and seemed impossibly mature and wise. When I was 26, I thought, I surely would be married, because 26 was when you became a grown-up. My job was to gather information about what it was like to work at the major consulting companies and write reports on them. I had never worked at a consulting company.
The stock market kept going up, and up, and up, and it seemed totally reasonable to think that this small, new company that had never been profitable would soon go public. Everyone was going public. My friend Sonya was working at Juno, which was a company that gave people free dial-up internet access in exchange for viewing ads, and when the company went public she made enough money to buy a car.
It was the golden age of websites that were ahead of their time: Kozmo and Urbanfetch were 1999’s Postmates; Webvan was 1999’s Instacart; GeoCities was 1999’s Facebook; Napster was 1999’s Spotify. We ordered pints of Ben & Jerry's to the office and marveled as they arrived, barely melting, within the hour. But for most people I knew, myself included, our daily lives hadn't totally caught up to what the digital future of 1999 promised. Most of us still didn't have cell phones; we recorded TV shows on VCRs; we had dial-up internet in our apartments, if we had it at all. People still had answering machines. We listened to music on Discmans.
And even as the stock market was making a lot of people very, very rich, the specter of Y2K — which threatened to shut down the world's computer networks because they had been programmed only for years beginning with "19" — loomed over us, an uncomfortable sign that the good times might soon be brought to an abrupt end. There were Y2K preppers who were convinced that the end of the world was nigh, brought on in large part by our over-reliance on technology. Most of us didn't actually think anything was going to happen, but there was always the smallest chance that it might.
My friend Marc had us over to his apartment for New Year's, a commercially zoned sixth-floor walkup on Bond Street. We ate carefully arranged appetizers and drank champagne and congratulated ourselves on not totally buying that the world was going to end. And yet, things were about to change more quickly than we knew.
In March, the stock market crashed. No one was sure what it meant — was this really the end? It turned out that it was. By the end of that summer, most of the people at the New Year's Eve party had scattered: I quit my job and went back to Philadelphia for graduate school, just as a bunch of people at my dot-com job got laid off. Things only got worse in November, when the presidential election ended with no clear winner, and then the next year there was 9/11. Any of the hope and optimism and progress left over from 1999 had by then officially been snuffed out by fear. It's hard, now, not to think that we didn't deserve 1999. It was a year that was simply too good for this world.