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5 Roving NEW YORK CITY, 2001

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Two weeks after college graduation, I took a one-way flight to New York with no job, no apartment, and a stack of clips from the Daily Texan. I’d saved some bat mitzvah money and what I’d made working in a snow cone stand off Barton Springs Road in Austin.

I temped all over Midtown, insurance offices and nonprofits mostly. Before work, I would run around Midtown in my suit and tennis shoes and drop off my stack of clips with the mailrooms or security desks at Newsweek, Time, Fortune, etc. A month later, I got a job as a rover at Condé Nast, the publisher of magazines like GQ, Vogue, Vanity Fair, and the New Yorker.

Condé Nast rovers were sort of like temps except that they had six months of steady work. We ranked beneath interns—who almost all had parents on the Upper East Side and attended a Seven Sisters school—but slightly above the outside temping agency I’d been working for. We had half a year to impress editors and publishers, demonstrating our efficiency at cleaning out closets, changing coffee filters, or picking up dry cleaning. Occasionally, we got to answer a phone. If no one wanted to hire us after six months, the gig was up and the program would be replenished with a new crop of desperate, broke aspiring magazine writers.

We all wanted our chance to temp at the New Yorker and Vanity Fair, but those magazines rarely asked for rovers. Mostly, we helped executives on the terrifying corporate floor, as white and sterile as a hospital, and were rotated in at magazines like Brides, Self, and Allure. One senior editor told me during an interview for a job labeled “beauty closet organizer” that “the best part about working at Allure is that it’s like a sorority.” Another asked if I would describe myself as a “makeup junkie,” as if one look at my almost-bare face didn’t answer that question.

Every day at Condé Nast was an education, though not necessarily the one I thought I’d be getting.

I was opening mail on the corporate floor for a creative director, a towering, hulking bachelor who wore ascots and had me print out all his emails and then transcribe his scribbles in No. 2 pencil in the replies. I got to a package containing a heavy Lucite box full of sand and aqua seashells, an invitation to a party in Montauk with the Sex and the City cast. He told me to RSVP no, adding, “But do me a favor. Find out if that actress who plays Charlotte is single.” I asked, in the docile voice of domestic help, if I could go to the party in his place.

“How are you going to get to Montauk?”

“Uh, well, I’ll take the bus.” I had no idea that Montauk sat at the tippy-tip end of Long Island.

“You’re gonna take the bus? To a Peggy Siegal party?” Ascot said. He laughed, more amused than irritated, and walked back into his office with the cream-colored carpet and the two white leather bucket chairs that I once heard his assistant describe as “the Herman Millers.” The furniture had a name, and I didn’t.

The one time that I’d rotated into Vogue, helping to organize the small closet converted into an office and library for the magazine’s fact-checkers, I’d worn my brand-new pair of UGG boots. Anna Wintour walked by the closet, paused, and behind her black glasses, fixated on the furry brown boots that I’d spent half my paycheck on. I never wore the UGGs again.

I’d been crashing at my college boyfriend Russ’s place in Bed-Stuy. Back in Austin, Russ and I had bonded over our love of Midnight Cowboy, each of us waxing poetic on its artistic subtleties and our own dreams of moving to New York. I should’ve known the relationship was doomed given that this movie, the ultimate testament to big-city failure, was what brought us together. Russ had an internship at the Nation that paid a stipend of $150 a week, and he liked to remind me regularly that I worked at lightweight capitalist rags and that he was the serious journalist in the relationship.

Fifteen years later, a Bernie Sanders supporter read my biography online and called me “a gruesome cross between Midnight Cowboy and Working Girl.” Pretty much. I’m brand spankin’ new in this here town and I was hopin’ to get a look at the Statue of Liberty …

MY BOSS AT Condé Nast had me come into the office the morning of September 12, 2001. I walked through a nearly deserted Times Square. I tried to remind this editor that no planes were flying, but she was adamant that she get to a photo shoot in Paris.

On my way to the office, Russ finally called. Other than a brief phone call the day before when we both had to evacuate our Midtown offices, I hadn’t heard from him and was starting to worry. He was driving his Honda Civic from its alternate-side parking spot in Fort Greene all the way back to the driveway of his mom’s house in Tulsa, presumably listening to Dostoyevsky on tape. He said he was already in Missouri and had decided to move back to Austin. He’d been the only person I really knew in New York, and he’d abandoned me.

In that first year, just existing in New York exhausted me. I always got on an express train when I needed a local, watching fifteen superfluous stops fly by. I couldn’t walk three blocks without getting stopped by Greenpeace volunteers or some man with a clipboard who wanted to ask me a question about my hair. Not wanting to be rude, I’d always stop. No, I don’t have a perm. No, does it look like I use a deep conditioner?

On most nights, I’d collapse, fall asleep fully clothed with the lights on. I’d wake up between the hours of 2:00 a.m. and 6:00 a.m. in a pile of saliva, the sound of sirens outside and the shape of the links from my silver Seiko imprinted on my cheek.

FIVE MONTHS AND three weeks into my rovership, I got my first full-time job in New York. I would be the editorial assistant to the garden editor at House & Garden magazine. In the interview, Garden Editor, a fashionably malnourished redhead who wore fishnet stockings and leather skirts, had growled a little when I complimented her leopard-print blouse. “Careful,” she said. “It’s a jungle out there.” Her husband would leave messages like “Tell her I’ll be home at six and will need something hot to eat and cold to drink …”

My duties included running to the Flower District on Twenty-Eighth Street each morning, where the sidewalks become an urban jungle of houseplants and cut flowers that supply the city’s restaurants and hotels and penthouses.

I once got on the Condé Nast elevator hauling cherry blossom branches wrapped in butcher paper when an airy ballerina of a girl about my age strode on, an Hermès Birkin bag slung over her forearm. I only identified this purse—and its $10,000 price tag and waiting list—because of the week I’d spent in the fact-checking closet at Vogue.

“Oh my God, I love your bag. Is it new?” another gazelle of a girl asked.

“No,” the ballerina replied. “I got it like a week ago.”

I tried to time my commute so that I could share the elevator with New Yorker editor David Remnick. Stalker-like, I craved even the tiniest reminder (the back of a brown head of hair) that my dream was still in my grasp.

One time, I stepped off on the eighth floor, with the purple House & Garden awnings, wearing my usual brown plastic banana clip and thinking about my illustrious future writing gig at the New Yorker. When the doors started to close, I overheard a woman announce to the packed elevator, “Okay, who told her she could wear her hair like that?”

Garden Editor would disappear for weeks to scout luscious private grounds in England and France and Morocco. She’d come back with a Longchamp tote stuffed with receipts for me to file and reams of film for me to develop into slides and arrange by theme (“Tuscan,” “xeriscape,” “Cape Cod”). She’d then present the hundreds of photos, which looked identical to the untrained eye, to the editor in chief, who would deem the gardens sufficiently tony (or not) to earn a spread in the magazine.

One afternoon I was arranging the slides into plastic sleeves, and after fifteen images of topiaries and a couple of bonsai, I landed on photos of the garden editor sprawled out naked, posing seductively for Mr. Hot-to-Eat.

In retrospect, I could’ve handled the situation more professionally, but I’ve never claimed to be a good editorial assistant. My gasp must’ve come out louder than I intended because a crowd of colleagues assembled around my cubicle. They held the slides now scattered over my desk up to the light howling that the garden editor “isn’t a real redhead after all.”

It was at that exact moment that Editor in Chief walked by and set her Siberian husky–like eyes on me as if I were some game animal she wanted to mount to the wall of her Pelham colonial.

She tried to have me fired for being “indiscreet” and embarrassing the garden editor. Luckily, the managing editor took pity on me (or anticipated a workplace lawsuit) and talked the editor in chief out of it.

I needed the paycheck and the health insurance, but part of me wished she had fired me so I could’ve filed for unemployment. My roommate at the time had just landed a real writing gig at Variety after being laid off from his job at AOL’s Moviefone. (He’d imitated the languid voice that reads showtimes: “To file for unemployment, press 1. To clear out your cubicle, press 2 …”) I envisioned parlaying unemployment into writing an explosive tell-all in New York magazine or the New York Observer called “The Garden Editor’s Bush.”

I knew my time at House & Garden was up when James Truman, the Condé Nast editorial director who would soon resign to bum around Andalusia and continue his studies with Tibetan Buddhists, flipped through a rough copy of the May issue and instructed Editor in Chief to swap out the cover story for a tiny blurb I wrote on a Chelsea flower shop that stuffed carnations into discarded Café Bustelo cans. This so infuriated Editor in Chief that she sent around a note reminding the entire staff (cc’ing me) that editorial assistants should under no circumstances be allowed to write.

I printed out the email and tucked it in my battered copy of A Confederacy of Dunces, which sat on my new IKEA bookshelf along with two volumes of poetry by Elizabeth Bishop and Isaac Babel’s Complete Works, which I’d borrowed from Russ and never given back.

The dunces, all in confederacy against me …

I TOOK A pay cut to work for a fancy literary agent who wore black leather pants and was on a strict South Beach diet. She’d email two words, “Protein Run,” and off I’d go to buy her hard-boiled eggs or almonds.

Every Friday we had to print out all our email correspondence from the week, and she’d hand the pages back to us on Monday marked up in red ink where she’d fixed typos and stylistic errors. Or, in my case, she explained at length why it was inappropriate to ask the agency’s clients for career advice. She had a point, but the only reason that I wanted the job was because her roster of authors included some of my journalistic heroes.

“You can do that. I mean, we all do that, but don’t ever include it in the correspondence. Duh,” another assistant in the Park Avenue office told me. She knew about my screwup because in addition to Literary Agent editing our emails, her five or so other employees all had to read each other’s marked-up correspondence. This led to grammatical shaming in the break room.

“Can you believe he used the passive voice in a message to Knopf ?” this same assistant said as she showed me how to arrange a hamburger patty on a bed of lettuce as Literary Agent liked. “You’d never think he was a Rhodes scholar.”

Just when I was starting to appreciate this semantic sadism as a useful crash course in email writing, Literary Agent fired me. She thought I’d stolen office supplies, which wasn’t technically true. She asked me to order twelve of her preferred purple highlighters and instead I’d accidentally ordered twelve cases (each of which contained ten highlighters). Paranoid she’d see this Mount Everest of purple in the tiny supply closet and erupt, I took ten of the cases home and put them under the bed figuring I’d gradually restock the office supply with this stash. But as I tried to explain this, Literary Agent just put up her hand in a please-stop-talking position. Ten years later, I was still pulling purple highlighters from underneath my bed.

I applied for assistant positions at Cosmo, the Economist, the Nation, Redbook, InStyle, House Beautiful, and Martha Stewart Living. I interviewed to be Lloyd Grove’s research assistant for his gossip column at the Daily News. (I heard he preferred young female assistants.) But he took one look at me and could tell I didn’t know East Hampton from East Rutherford.

I waited and waited, clutching a faux-leather padfolio filled with clips from the Daily Texan, in the lobby of the old Times building. A political reporter whom my sister met through a mutual friend said she’d meet with me, but she never showed. After an hour, a security guard told me I had to leave.

I scrapped around for freelance writing jobs. I reviewed Greek restaurants in Queens and wrote a story for Time Out about things you can buy for a dollar in New York. I worked part-time out of some rich lady’s Upper East Side basement fact-checking a guidebook to interior decorators that she published for her friends. I applied to the Columbia University Graduate School of Journalism even though it would’ve taken me the rest of my adult life to pay for a single semester. I was wait-listed. I became an early adopter of Internet trolling, blasting the whores in corporate media in manifestos that my new boyfriend (the homeless Italian with the camcorder) published on his blog. If ya can’t join ’em, troll ’em. I considered starting a dog-walking business. You know it’s bad when scooping poop off sidewalks sounds promising.

Finally, in the dead of February when I was almost broke, I went to the Strand bookstore and bought a lightly used copy of LSAT for Dummies. That same night, over a dinner of yogurt and instant ramen, I got a call from John Bussey, the foreign editor at the Wall Street Journal.

Chasing Hillary

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