Jennifer Romolini | Weird in a World That’s Not | Harper Business | June 2017 | 10 minutes (2,475 words)

Long before author Jennifer Romolini’s name appeared high up on the mastheads of publications such as Time Out NY, Tina Brown’s Talk Magazine, and Lucky, and websites like Yahoo Shine, Hello Giggles and Shondaland, she struggled to find herself. She spent her early 20s waitressing in restaurants and hotels, and was soon rushed by a pregnancy that ultimately wouldn’t last into marriage that wouldn’t, either, with a summer fling who should probably have been no more than that. She felt lost and stuck. She felt limited by her working class upbringing with weird parents who fashioned themselves after the oddball parents in Bowie’s “Kooks,” and by her academic failures — mostly for lack of trying — first in high school, then in college, which she didn’t finish. A perennial misfit where ever life took her, she assumed doors would always be closed to her. But a few years later, after leaving her first husband, she committed to figuring out what she wanted, getting her life together, and finding a place for herself in a career she liked, without compromising who she was.

When she was struggling, none of the career books on the market quite spoke to her, or offered solutions for someone who’d never been on a traditional career track. Now, after years building her career as an editor, she’s decided to fill that void for younger women who find themselves in her old shoes. Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures, out today, is the book she wished she’d had — an interesting addition to the growing category of Misfit Lit, a hybrid of memoir and self-help. What follows is an excerpt, recommended by Longreads Essays Editor Sari Botton.

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My first waitressing job was at a nondescript Mexican restaurant on the lower level of a two-story strip mall on a six-lane “pike” in a nondescript Pennsylvania suburb right near a nondescript mall. We served chips and salsa and sizzling fajitas that would splatter onto the most tender parts of your neck as you balanced them high on a tray. Our house specialty was the Monstrita—a triple-serving margarita in a fishbowl-size glass with a deceptively delicate stem and the ability to get you plowed drunk within three sips. I was twenty when I got this job. I wore a black button-down man’s shirt and metallic purple bolo tie. I was wobbly and awkward and not very good. The restaurant was owned by two thirtysomething Indian men, Apu and Tushar, one short and short-tempered, one tall and stoic, both fundamentally kind.

I spilled drinks. I slipped and broke plates. I fucked up my orders and miscalculated my checks and at the end of the fourteen-hour shift, bolo tie askew, was called into the manager’s office.

During my first week on the floor, I had a day that was particularly bad. I was working a double shift, and during lunch I spilled hot coffee on a man who was deaf. This was because I had poor balance and did not know yet how to skillfully wield a tray but also because the man was deaf, did not know I was behind him, and leaned back into the coffee as if eager to be close to a heat source.

I hadn’t known you were supposed to tip the busboys, so they all hated me. As my shift progressed, all the tables in my section became dirty and nacho-strewn. Later that night I served warm chips from the wrong warm chips dispenser, the one outside, the one we were explicitly told NOT TO USE that night, and those chips turned out to have roaches in them. I spilled drinks. I slipped and broke plates. I fucked up my orders and miscalculated my checks and at the end of the fourteen-hour shift, bolo tie askew, was called into the manager’s office. I was sure I was going to be fired. Instead, after acknowledging the day’s disasters, Apu signaled to the bartender, who brought in two shots of tequila. He told me he knew I was trying. He said he thought I could and would get better. He told me I made the customers laugh. Then he held up the shot glass and cheered to better nights ahead. Though we both knew I’d fucked up, his approach was so empathetic and hopeful and focused on the positives, I have practiced this Apu-management method ever since.

Waiting tables was my main source of income for the next seven years.

Could I wrest the power from them, let them know—subtly—that they were misogynistic assholes, and still get a good tip? Could I make them think that the $95 bottle of wine was their idea?

It was the first thing in my life that gave me confidence that I could make my own way in the world. There was a hierarchy to waitressing, and I started climbing the ladder—fancier places paid more in tips and the conditions were less grueling, so I got fancy. I made Caesar salads tableside. I lit up flambés. I practiced opening champagne with a whisper and not a pop.

I learned French wines and French foods enough that I could recommend French wines and French foods. Waiting tables taught me how to talk to rich, educated people. It taught me how to move my body with strength and at least a semblance of grace. It gave me access to a sophisticated $40-an-entrée class that I would have never met otherwise. I would need to understand these people later in my career. I would need to know how to dine in places that sold $40 entrées.

For the most part, you get what you put into waitressing—the more you hustle, the more money you make. Waiting tables became the foundational education for everything I’d do in my professional life. The constant multitasking, the precision necessary to execute a meal, learning to perfect my timing and collaborate with a team—these were lessons I’d carry with me for years, and use even today. The family feeling of a restaurant, the feeling that you are all in it together, because you have to be, because you need each other to get the work done, is an apt model for team building in office jobs. Understanding the delicate ecosystem of a restaurant—who you need to take care of and give fucks about to give the customers the best experience and get the best tips—taught me how to navigate politics in big corporate jobs. In restaurants, I learned to flip power dynamics, like those of young female server versus table full of rich white businessmen. Could I wrest the power from them, let them know—subtly—that they were misogynistic assholes, and still get a good tip? Could I make them think that the $95 bottle of wine was their idea? How far could I push before it went too far, before it turned into a complaint about my “attitude”? (I got a lot of those complaints too.)

I worked in more than a dozen restaurants over the course of my career as a waitress. The first job that profoundly changed the direction of my life was at a big hotel chain with two dining establishments.

He was kind and normal, and he wanted to marry me. I was lost and sad and broke and felt like a freak. I said yes.

City Limits, the classier of the two, was all 1980s pink-and-gray banquettes and soft lighting and nowhere near a city, a space where the local politicians came to cheat on their spouses (hotel rooms upstairs!), where Larry “Bud” Melman once grabbed my ass (look him up), where La Toya Jackson conducted the world’s most boring conversation and ate only filet mignon. The Green Parrot was an all-you-could-eat pasta-and-crab-legs joint where bibs were provided, the gratuity was automatic, and your job as a server was to be the cleanup crew, shoveling discarded crab shells, spaghetti marinara, and blue-cheese-dressing-doused let-tuce into giant trash barrels without throwing up.

When you were a new employee at this hotel, they made you work the Sunday all-you-can-eat morning buffet; when you were really new or truly loathed, you had to work Mother’s Day brunch. There is no hell in the restaurant business like Mother’s Day brunch. Valentine’s Day, with all its forced love and romantic posturing and tables of two, sucks. New Year’s Eve, when the rest of the world is out wearing sequins and blowing horns, is a sad FOMO hell. But nothing is worse than Mother’s Day, with its reluctant-to-be-together families, barely-there grandmas, and feral kids running wild around hot drinks and making a mess of buffets. Mother’s Day brunch customers are not mimosa and chill people. This is obligatory dining, people who don’t want to be there, who aren’t used to eating out, who have an unusual amount of needs, run you ragged, and then leave terrible tips. This is the lowest, messiest, busiest, cheapest, complainiest the restaurant business gets.

And this, in the sexiest of places, is where I met my first husband.

My first husband was a cute hotshot hotel manager in a place where no one was cute and no one was a hotshot. He was the popular guy in high school who would have never dated me back then. He wore man shoes and double-breasted suits from Men’s Wearhouse in various shades of brown and listened to Rush in his convertible with the top down. We hung out for two months—–a distraction, an East Coast summer fling—–and then, when it would’ve been over, when we would’ve each moved on to people more our own kind, I got pregnant. He said he would marry me. He was kind and normal, and he wanted to marry me. I was lost and sad and broke and felt like a freak. I said yes.

Five months later we were married in a cavernous Catholic church in front of 150 of our parents’ closest friends. I wore a bride costume: white gloves, a giant satin-and-sequins dress from David’s Bridal and a crinoline veil spotted with faux pearls. Under my dress, I wore a pale-blue garter and an over-size sanitary pad. I was still bleeding from the miscarriage.

We spent the first few months of marriage in a small, stark town near the hotel where we worked. We rented an all-white one-bedroom apartment covered in indoor/outdoor gray carpet and furnished with leftover hotel furniture—brass and felted teal banquet chairs, a multicolored houndstooth-print sofa, bedside tables with the lamps attached. It was the setting a location scout would choose if the goal was to show characters slowly drifting into insanity, death by starkness-plus-ugliness. It was what we could afford. I picked up a second job during the day, working at a New Age coffee shop across the street from our apartment. I made cappuccinos and defrosted “grade-A” scones. I sold copies of The Alchemist. I led people to spirit animal workshops and tarot card readings in the events space up- stairs. For our first Christmas together, my husband bought me a vacuum cleaner. I wanted a bike. We did not know each other at all.

I was witness to other people’s lives, but I was not living my own, and that clarified the fact that I wanted one, more desperately than I even understood.

Later that year, in the first of a series of relocations we made to try to make things right between us—because I was sure making things right between us would make me right—we moved to the attic apartment of a two-hundred-year-old bed- and-breakfast that was originally a stagecoach stop and general store for Deadwood-type folks traveling from Philly into as-yet- uncivilized lands. We were hired as innkeepers, though my husband kept his regular job at, and a long commute to, the hotel where we’d met. We welcomed guests traveling through rural Pennsylvania, mostly in the summer, mostly old people in shorts. We gave them breakfast and, later, led them to the tavern downstairs where they could drink Grasshoppers and dine on dishes like prime rib or crab cakes in front of a fireplace. They said the inn was haunted. They asked if I’d seen the ghosts. I would have welcomed the company.

At night I waited tables at the restaurant downstairs. I worked with women in their forties and fifties, women who talked about their husbands and kids and goulash. It was seventeen miles to the nearest store. On our first anniversary, in the dead of winter, my husband worked late. I opened a bottle of wine and watched Love Connection reruns on our tiny TV, snow out the windows as far as you could see.

One afternoon late that summer, while I was dusting a sitting room, the inn’s main phone rang. It was my mother, calling to say she was excited about my upcoming move to Connecticut. I did not know I was moving to Connecticut. My husband had called her first to discuss his promotion—a relocation! Didn’t she think that was great? She did. I did not know what I felt anymore.

Three weeks later we moved to a hotel for business travelers in Stamford, Connecticut. My husband had been sent to fix its food and beverage department. We were put up in the hotel for a period of four months, though we’d stay six. As part of his employment package or maybe just to be nice, I was hired at the hotel’s revolving rooftop restaurant, Windows on the Sound, which was really Windows onto Interstate 95 with a sliver of water in the distance. Late at night, when I finished working, I would retire to our standard-size hotel room, order personal pan pizzas from the Express Pizza Hut downstairs, and eat them atop a floral-print bedspread on the king-size bed. There was no cable. We worked strange hours and were often up late. We watched a lot of Three’s Company and a lot of infomercials. My husband made three easy payments of $29.99 for a vibrating brush and a year’s supply of hair-growth shampoo in big cardboard boxes that took up most of our bathroom. He hung the instructional poster on the wall. The shampoo smelled like old perm, and so did our room. My husband’s job was more difficult than we’d imagined, or maybe he wasn’t as good at it as we’d thought. Either way, he worked seventy-hour weeks. I was often, almost always, alone.

There was TV and room service. There were conventions, weekends when the hotel was flooded with pharmacists, recovery groups, accountants, dentists. There was the hotel gym, but I never went. I waited on business travelers, lonely and awkward,

newspapers under their arms, before there were cell phones to keep humans company. During the day I nannied for the hotel general manager’s girlfriend’s kids, who had just moved to the hotel too. They lived in a suite on the twenty-second floor. The kids missed California, they missed their friends, they missed their dad. We were all strangers and nomads. The hotel restaurant revolved. Everything felt unmoored, like one day we could all float away.

When you work in the hospitality business, you are a voyeur, witnessing and even participating in some of the most intimate moments of people’s lives. I watched groups of female friends celebrate birthdays together, hugging and gossiping and conspiring, getting topply and tipsy by the end of the meal. I watched anniversary weekends, men carrying women they’d loved for years over standard-hotel-room thresholds. I observed terrible and wonderful first dates, all tense until the wine started flowing, until someone made a good joke and someone else laughed. I served big family graduation and retirement dinners, wedding and baby showers, generations in attendance. I helped orchestrate elaborate engagements—can you put the ring on the cake, can you put it in her glass of champagne, can you serve it, and just it, for dessert. I sang “Happy Birthday” to beautiful women whose husbands signaled me nervously, tried to give the heads-up without their wives seeing, even though they nearly always did. These celebrations, these moments of joy, affection, connection, only made my loneliness more profound. I was tethered to a man I increasingly understood I did not love, living in strange places I did not like, around people I did not know. I was witness to other people’s lives, but I was not living my own, and that clarified the fact that I wanted one, more desperately than I even understood.

We ran up the bill in the hotel room—too much room service, too many movies, too many long-distance calls, and, as I’d find out later, too much porn. We overstayed our welcome. We were supposed to find an apartment, but we never did. My husband got another job and we moved back to Pennsylvania, to another rural hotel, this one next to the QVC studio, where Joan Rivers would come and stay with her tiny dog and sell jewelry on TV. My husband sometimes walked her dog. He said she was nicer than she was on TV. He said Victoria Principal was a bitch, though. These are the things you remember.

Soon after, I’d be sitting in the driveway, trying to leave. Soon after that, I pulled myself together—pretty much for good.

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Excerpted from Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures, by Jennifer Romolini. Copyright © 2017 by Jennifer Romolini. With permission of the publisher, Harper Business. All rights reserved.