Starting From the Bottom

By Jenna Wortham


I didn’t start out wanting to be a journalist, let alone one who worked at one of the biggest publications in the world. As the first person in my family to go to a reputable, sleepaway, four-year university, my career goals were simple. I wanted a job with a salary and good benefits, especially dental, because I have a terrible sweet tooth. But it didn’t work out that way, at least not at first. Everything about college baffled me; nothing I studied or did adequately prepared me for figuring out how to carve out a successful life for myself after graduation.

Most of my friends had five-year plans; some even claimed to have ten-year plans. Many had at least chosen a professional category to pursue: law, medicine, business. Me, I made the plan to have no plan. I was loose, almost pathologically determined not to commit to something too soon. Sometimes that was terrifying. I’d be listening to my pre-med friends talking about their top picks for residency, and a wave of panic would subsume me, and I would spend the rest of the day dazed, not sure if I should be doing what they were doing, if I was making a series of terrible, tactical life errors that would haunt me for the rest of my days. But I’d seen enough Felicity to know that it would take some time to figure out my life plan, and I felt confident that one would materialize eventually. I had gotten myself into college, and if I left with a degree in hand, that felt good enough for me, so I focused on what I considered to be the colloquial college experience instead.

Most of my friends had five-year plans; some even claimed to have ten-year plans. Me, I made the plan to have no plan.

I signed up for a sculpture class that mostly involved sneaking into a local scrap yard late at night and picking through junk and old electronics for things we might fashion into other things. I lived with a whole mess of girls in a tiny apartment right above four cute engineers who liked to take our door off and use it to play beer pong. I signed up for swim class and then dropped out. I signed up for crew and then dropped out. The unending options were unnerving, but I had a blind confidence that my haphazard process of eliminating subjects, concepts, and areas of study would somehow, eventually, deposit me at the foot of my future career and path. I took a class on riot grrrl zines taught by a grad student who would knit hats during class and hand out mixtapes of Bratmobile songs. I bounced from the biology department to the anthropology department and later applied for a semester abroad in London studying public health. When I came back, I moved off campus with my boyfriend and enrolled in graduate classes in grassroots media.

But as graduation slowly started to solidify from a murky concept into a rapidly approaching date, I began to realize that the degree that I was going to wind up with — a combination of biology, lit classes, and anthropology — didn’t seem to be a natural fit for anything — interesting or otherwise — on the job market. At night, anxiety made camp in my body, keeping me awake as I fretted over what I could do to make money and where I would live.

At night, anxiety made camp in my body, keeping me awake as I fretted over what I could do to make money and where I would live.

Some of my classmates and friends were filling out applications for the Peace Corps and Teach For America; others were preparing for graduate school. Most had gotten help securing an office job in their hometowns and were preparing to move home. None of it appealed to me. College had taught me how to properly prepare ramen and hot chocolate in a hot pot balanced on a plastic crate, how to use new tools like Napster, Kazaa, the delicate balance of winning an argument in lecture that both charmed the professor and didn’t annoy my peers, the joy of diner food at two a.m., and the art of crafting the perfect away message to leave on IM while away from my computer. Social cultivation, self-presentation, cultural interests, yes. Professional direction or any sense of how to use what I’d learned over the last four years, no. Facebook was just starting to catch on around college campuses and the FOMO was intense and real as people started posting updates about new jobs or European summer trips. I couldn’t pin my future down in that exact moment, so I made the decision to delay it. I’d always been able to figure out a plan, and I knew that money was the key to future independence. The thing is, I’d had all kinds of jobs before, but none were jobs that I wanted to return to after graduation. But I figured working was better than not working, so I set about getting a kind of job that wouldn’t necessarily be one that I’d have forever — just for the near term. That decision not to rush into a decision, the uncertainty of continuing to cherry-pick between classes and sampling different ideas and potential career paths, seemed terrifying, but in hindsight, it helped establish my early twenties to make way for the leaps and risks that I would have to make later on as my career began to take shape. I’d always worked, I’d always hustled. And that instinct to get work and build up some momentum, even if I didn’t yet have a clear sense toward what, would wind up serving me as well as, if not better than, the sum of all the classes I’d sat through and papers I’d handed in.

I figured working was better than not working.

During my last year of school at the University of Virginia, I was spending most of my time downtown, away from campus, and I had gotten to know a few servers from the restaurant scene. I’d heard from a few of them that business was good. They sometimes made as much as three hundred dollars on a good night, which was my share of the rent at the time, and it seemed too good to pass up. I was hired at the first place I applied, a super-fancy French restaurant known for its handmade pastas and locavore approach even before that was a popular trend, mostly because everyone else had quit the day I walked in. In hindsight, that should have been a red flag, but I was excited by the prospect of a new challenge, and of course, the money. I remember standing there, sparse résumé in hand, when Roman, the bartender-slash-manager, asked me if I was up for helping him run the restaurant that night. They were expecting a full house of people and we’d make bank, he promised, since he and I would be the only two waiters splitting tips. I agreed, and he tossed me a black server apron and told me to start setting tables. Before that night, I hadn’t done more than have a few friends over for dinner, and I was wholly unprepared to gracefully and elegantly take care of an entire dining room asking for recommendations on dishes like sweetbreads and ordering cappuccinos that I had to make myself, on a rickety machine in the back. The chaos was so unnerving, so extreme, that I blacked out most of the night.

The chaos was so unnerving, so extreme, that I blacked out most of the night.

I can remember a few things, in no particular order: I sweated through my entire outfit, spilled hot tea on a guy that I recognized from around school, and corked a very expensive bottle of wine that I tried to open tableside. There’s no real way to quantify the hellish stress of standing next to a table that is quietly debating whether to share an entrée or get two different ones to try while the people across the room are glaring at you to come take their drink order. The ever-evolving mathematics of orchestrating the arrival of food, drinks, checks, and new customers was exhilarating and exhausting. It was like a never-ending game of Diner Dash, relentless and insufferable. But I didn’t get any orders wrong, and I managed to maintain my cool over the course of the night. After the last customer left, we locked up and opened a bottle of champagne and toasted ourselves for not going down in flames. That night, I’m pretty sure I pocketed enough money to cover my rent, and a nice amount of cash to cover expenses for a few weeks. It was liberating in a way that my college classes had not been until that point, and the crisp bills felt like a step toward something else after college, savings to travel, a safety net to cover my bills while I ran errands, or, who knows, got hired to do part-time work for a photographer or a filmmaker, perhaps. And I was done in time to go meet my friends for last call. I was hooked.

Until that moment, nothing in college made much sense. I found the entire four-year process to be such a mysterious ritual that waitressing, by comparison, was a relief. I struggled to fit into the collegiate dance of a southern school that counted wearing ties and sundresses to football games among one of its traditions. It was a special breed of performative adulthood I wasn’t quite ready for — am still probably not ready for. But waitressing was different. It was something I could figure out, a game that I had the instructions for. And it was hard, but also simple. If you worked hard enough and paid attention, you could do anything, make anything work. You could handle any table, any crisis, so long as you kept your wits about you, and there was something incredibly reassuring about that. The hustle also appealed to me, as did the mental calculus that you have to do for each table to plot out the course of their meal. Of course, then there was the money, which felt like a freedom from the servitude of being a struggling college student.

People’s reactions to my announcement became a Rorschach test that was fairly accurate at predicting the length of time we’d be in touch after graduation.

Most people I worked with weren’t planning on being servers forever. Some were in school like me; others were using the money to supplement their day job as artists or dancers. I had a fantasy of a future self that worked as a photographer, a social activist, a documentary filmmaker, a vaccine researcher, or even as a chemist. But the clearer it became that I had no idea what to do after college, the more appealing waitressing as a stopgap became. A reliable job and skill set that would be applicable in any city I landed in sounded like a smart way to start my postgraduation life. I knew it paid well, and I would have my days free to intern, freelance, or do odd jobs. And so I shook Roman’s hand and accepted that job and others like it while I figured out how to be an adult human and turn the various side projects and freelance gigs I was doing into something resembling a career. The job quickly became a priority, pulling me away from college dances and parties, but I didn’t mind. I started telling people that I was waitressing to save up enough money to go to California, which eventually became true. People’s reactions to my announcement became a Rorschach test that was fairly accurate at predicting the length of time we’d be in touch after graduation. It sounded cool enough to a few of my closest friends who decided to do the same, and we all began to prepare ourselves for a great migration out West. We dreamed of open skies, a chilled-out vibe, and the space to become fully realized, whatever we thought that meant. It wasn’t much of a plan but it felt like a better plan that most people had, which involved getting a regular office job. But by this time, my grassroots publishing class had begun to work its way under my skin, and I liked the way it took root there. I pictured myself running a similar enterprise someday. We published a magazine each semester, and planning out the issues, the front-of-the-book stories, features, and profiles that we would include was exciting in a way I didn’t even know was possible. In those classes, the beginnings of an idea took shape, if only I could figure out how to finance it. The reality that I had spent the last four years doing everything but studying literature, writing, and reading started to weigh on me, even though all of those areas interested me the most. But I figured I would stockpile cash, leather jackets, and skinny jeans, move to a city, live in a one-room apartment, and work and intern for free in exchange for experience points. Simple enough, right?

It turned out that waitressing was my last first job, the one that would carry me through until I landed at the New York Times.

Waitressing, first in Virginia, and then in San Francisco, was much more than a buffer, much more than a cushion of cash that paid the bills and allowed me to afford small animal comforts like nice bottles of wine and occasional overnight trips down the coast. Learning to collaborate with strangers, along with the ability to interface with other people — read them, anticipate their reactions, learn how to adapt and react to almost any situation — better prepared me for the kind of future that I always pictured that I wanted. It was something I’d never expected to learn from a restaurant. I worried that my lack of a serious-sounding job title or fellowship would harm my chances at success in the future, but it turned out that waitressing was my last first job, the one that would carry me through until I landed at the New York Times. I didn’t realize it at the time, but I learned almost everything I needed to know to be a successful human while working in restaurants, possibly even more than I learned in college. The bone-breaking hard work of hoisting trays of food and glasses and the relentless charm and poise that is required for the service industry primed me for years of long hours interning for little to no money and a willingness and openness to experiences that would help me inch closer to the dream goal of someday running or writing for a magazine. It’s the one job of the half dozen I’ve had that I miss on occasion.

People ask me all the time for career advice. They’re interested in figuring out how to carve out their own path, whether forging a future in a world that is rapidly shifting — often beneath their feet — is possible , and how much weight a traditional education carries in a world that is increasingly defined by skills and expertise that is still being shaped. Most people are worried that they aren’t doing enough or that their social or online footprint isn’t big enough or distinguished enough. When you’re first starting out, you probably won’t get the job you want. You probably don’t even know what the job you will be happiest with looks like yet because, chances are, it isn’t around yet. Or its definition will be so fluid and flux it doesn’t warrant proper categorization or title. And it’ll probably take awhile to get it.

I learned almost everything I needed to know to be a successful human while working in restaurants, possibly even more than I learned in college.

Ten years ago, I thought I’d be a magazine writer or a columnist. Today, I’m a business reporter and sometimes a columnist, a videographer, a producer. I do all kinds of things I never thought I would get to do, and it changes constantly because the field I work in is evolving underneath my feet. Being lean, being flexible, being agile enough to evolve has helped keep me afloat. Paying attention to my environment and making sure I’m a part of it, rather than a tourist in it, has also helped. Everyone has their own path, and not all paths look alike. This gets harder and harder to remember when we are all preening and performing on social media, celebrating the highlights — new jobs, promotions, the lists we were recognized on and the articles about our successes — and ignoring the lowlights. The struggle is real, and it touches everyone at some point, but we’re inclined to ignore it on the way up. It’s easier that way. But comparing myself to other people has never gotten me anywhere — I never wanted to be like other people, and that’s still true, even now. I didn’t start out with much by way of external resources — I didn’t come from family money, or resources, or anything else that might help me get a jump in the media world. But I was fairly confident that I could figure out anything on the fly (and never let on otherwise) and that I could do it beautifully. Those were the stories I told myself to live, to keep my head above water when it felt like I should give up or maybe try something else. I trusted my gut, I trusted my instinct, and I trusted that I could make it work.

Jenna Wortham is a technology reporter for the New York Times. She currently lives in Brooklyn. This is an excerpt from her essay, “Starting from the Bottom,” from The 10 Habits of Highly Successful Women on Amazon Kindle.