Uncanny Valley

by Anna Wiener

  Everyone I knew in San Francisco had already left. Our college class had graduated straight into a recession, and while most of us trudged to New York or Boston to compete for unpaid internships and other scraps of a ravaged economy, those who moved west refused to bend to despair. They chose instead to hide out for a while, work on their art. They lived in sun-flooded apartments, took part-time service jobs, and had complicated, consuming social lives. They freely experimented with hallucinogens and polyamory; smoked weed and slept in and day-drank; went to BDSM parties and wolfed burritos afterward. They started bands and did occasional sex work. They spent weekends in the mountains or the woods or on the beach, camping and hiking and participating in other wholesome activities that we made fun of back in New York.

  This utopia was short-lived. It was being replaced by a late-capitalist hellscape, my friends reported. Rents were spiking. Art galleries and music venues were closing. Bars were overrun with men in their twenties wearing corporate-branded T-shirts, men who never finished their beers and complained whenever anyone on the sidewalk smoked a cigarette too close to the door. Men who wore stability running shoes to nightclubs. Men who said “K” instead of “thousand.”

  Dating websites were flooded with milquetoast strivers who earnestly listed business-management guides among their favorite books and arrived at dinner wearing backpacks stamped with the names of their employers. Young CEOs were showing up to sex parties expecting to play only with other young CEOs. My friends, covered in glitter and wearing tiny nut-hammocks and rolling on ecstasy, found themselves marching in the annual Pride parade alongside primary-colored, brand-consistent, family-friendly floats designed by heterosexual digital-marketing managers.

  The city had begun to bend to the on-demand desires of recent college graduates with plump bank accounts. Even Oakland was becoming unaffordable for artists and writers working as loosely credentialed yoga instructors or grocery store cashiers. There weren’t any jobs, my friends said, unless you wanted to work for a tech company. It went without saying that none of them did. Within a few years, they departed for gentrifying neighborhoods in New Orleans or Los Angeles, or found their way to graduate school, their flight paths and cross-country road trips doing double duty as funeral marches for a beloved city that, they all assured me, no longer existed.

  When I traveled to San Francisco in the spring, to interview for a customer-support position at a data analytics startup, I didn’t mention it to my ex–Bay Area friends. I dreaded how they would react if they knew I was angling for a job in the tech industry, that I had even a shred of interest in joining the people on whom they blamed their displacement—the people who had ruined their fun. I took the train from the airport into the city, feeling treacherous and estranged.

  Using the millennial-friendly platform for renting strangers’ bedrooms, I had booked a room in the Mission, in an apartment that belonged to a couple in their mid-fifties. It was my first time using the app, and as I stood on the front steps of an ornate Victorian, I felt like an orphan of nineteenth-century literature, a child on the brink of a new adventure. Welcome home, the home-sharing platform’s marketing materials had gushed, exuding familial warmth with bright, bold colors. But while the website emphasized community, coziness, a richer life through new connections and novel experiences, my hosts greeted me coolly—a reminder that this was, above all, a transaction.

  As the husband showed me around my room—guest towels in the hope chest, lemon tree in the backyard—he asked what had brought me to town. I explained with some trepidation that I was there to interview at a startup. I knew that the neighborhood had long been an enclave for artists, activists, and other groups without enough money to hold their own in housing court. I wanted to be sensitive. He nodded knowingly, without judgment, and shrugged. “We host full-time,” he said. “I guess you could say we work for a startup, too.”

  Could I? He and his wife had both quit their day jobs, in the nonprofit sector, to provide the trappings of an authentic urban experience—different enough to be interesting, but generic enough to be comfortable—to tourists and interlopers like me. They slept in the basement. They weren’t employees. They were part of the product.

  It was my first time paying to stay with strangers. The apartment was clean and welcoming, full of overstuffed furniture and bowls of fruit, but I didn’t know whether relaxing with a book on the sofa or borrowing kitchen implements to slice a ripe peach would be considered a breach of the home-sharing platform’s terms of service—I’d only booked a room, after all. The policy had extensively covered the company’s liability but didn’t offer any specifics on how to behave. To play it safe, I walked carefully between my bedroom and the bathroom, as if the hallway were a grooved track—as if I were trespassing, intruding on a family and a life that did not belong to me.

  * * *

  The interview had been arranged with the help of the e-book startup’s CEO, who advised that big data was a hot space. According to him, the analytics startup—just four years old, founded by college dropouts—had already infiltrated the market with impressive speed and ferocity. The company had twelve million dollars in venture funding, thousands of customers, and seventeen employees. “Our investors say they’re the next unicorn,” the e-book startup’s CEO had enthused, tipping back in his chair. “It’s a rocket ship.” It was easy to get me to want something.

  I was not particularly excited about customer support, but it was an entry-level job that required no programming knowledge. As a sociology major with a background in literary fiction and three months of experience in snack procurement, I assumed I was not in a position to be picky. The e-book startup’s cofounders had been adamant that customer support was a temporary state. If I hustled, all three of them agreed, I would quickly find myself in a more interesting, autonomous, impressive role. I didn’t know that in tech, qualifications—at least the traditional ones, like advanced degrees or experience—were irrelevant when superseded by cheerful determination. I was still behaving like a young professional in a world where dues-paying mattered.

  In an effort to hype myself up, I developed the theory, however flimsy, that analytics was a natural extension of my liberal arts education. The e-book startup had used the analytics software to track our alpha users through the app, and I had enjoyed looking at some of the data: what our investors were reading, and abandoning; whether or not people read public-domain books with cover art designed by the CPO, which we had added to bolster the library. In a certain light, I tried to convince myself, business analytics could be seen as a form of applied sociology.

  The night before the interview, in the privacy of my rental bedroom, I read interviews and puff pieces about the analytics startup’s cofounders, now twenty-four and twenty-five years old. According to the tech blogs, they’d just been two underage students with one Silicon Valley internship between them, and a smart, practical, easily pivotable dream of a world driven by the power of big data. This was a dream that greatly appealed to the admissions committee of a renowned seed accelerator in Mountain View, which offered funding and connections in exchange for a 7 percent stake. The accelerator’s slogan was an inspirational exhortation to founders to make things people wanted—not, I noted, needed. It boasted a handful of success stories—a grocery-delivery app, a livestreaming site, the home-sharing platform—as well as dozens of failures. The CEO and technical founder had left their college in the Southwest to join the accelerator, then enrolled full-time in the ecosystem.

  Several months prior, a tech blog had published an article announcing the analytics startup’s first major fund-raising round of ten million dollars. When asked how he would spend the new funding, the CEO made his priorities clear: he would pay the first hundred employees far above market, he said, and spoil current employees to retain them. This was the language of customer acquisition, but I didn’t know. I didn’t think at all about the stratification, either; how the hundred-and-first employee might feel. I’d never worked an
ywhere with a hundred people—I’d never worked anywhere with twenty. I’d certainly never worked anywhere that wanted to spoil its employees and had the means to do it. Generous, I thought. I found the tenacity winning.

  * * *

  When I arrived at the analytics startup’s headquarters, I was surprised to find that the whole enterprise was peanut-sized. The office, however, was huge—at least seven thousand square feet, with a polished-concrete floor, and mostly unfurnished. About fifteen employees were clustered together at the far end of the room, all gazing deeply into monitors. Some stood at elevated desks, legs spread sturdily, feet cushioned by little rubber mats. Every work space had its own colorful clutter: pots of succulents and other dying plants, anime figurines and stacks of books, bottles of nice liquor. On one was perched an obelisk of empty cans, husks of the same high-caffeine energy drink. The open-plan setup made it look like a classroom. No one there looked over the age of thirty.

  I stood in the doorway and counted the women. There were three. They wore jeans and sneakers, oversized cardigans over T-shirts. I had dressed carefully, in a blue shift, heeled boots, and a thin blazer. It was what I always wore to interviews, and I thought it signaled professionalism and seriousness. In publishing, an ensemble like this was nice, but still dowdy enough to be nonthreatening. Inside the startup, I felt like a narc. I shrugged off the blazer as discreetly as possible and stuffed it into my tote bag.

  The first interview was with the manager of the Solutions team, the customer-facing division. He was jolly and hirsute, wearing faded jeans and a company T-shirt that declared I AM DATA DRIVEN. I resisted asking if it needed a hyphen. He sat down in one of the ergonomic desk chairs, leaned back, and bounced lightly, like a baby. Through the glass door of the conference room, on which was taped a handwritten sign designating it THE PENTAGON, I watched a wiry man in a plaid shirt wiggle past on a RipStik, waving one arm for balance and shouting enthusiastically into a golden telephone receiver.

  The solutions manager placed his elbows on the table and leaned toward me, explaining that we would be going through a series of questions together so I could demonstrate how I problem-solved. “So,” he said, as if he were asking me to let him in on a secret, “how would you calculate the number of people who work for the United States Postal Service?” We sat in silence for a moment. I wouldn’t, I thought; I would look it up on the internet. I wondered if perhaps this was actually a test of my tolerance for bullshit and inefficiency—if the sassy response could also be the right one. I had no idea what the solutions manager wanted. Then he handed me a marker and pointed toward the whiteboard. “Why don’t you get up on the board and show me how you’d work it out?” he asked. It wasn’t a suggestion.

  In the four hours that followed, the solutions manager and the wiry man I had earlier seen cruising past, a sales engineer, walked me through a series of questions and puzzles. The sales engineer seemed to be about my age, and had an unaffected drawl and manic, infectious energy. His speech was littered with folksy aphorisms. “Butter my biscuits,” he said, when I complimented his oversized belt buckle. “Now we’re cooking with gas,” he said, teaching me how to reverse a string on the whiteboard.

  Both the sales engineer and the solutions manager exclusively referred to the data-analytics software as “the tool.” Both of them asked questions that were self-conscious and infuriating. “What’s the hardest thing you’ve ever done?” asked the solutions manager, twisting his wedding ring around and around. “How would you explain the tool to your grandmother?”

  “How would you describe the internet to a medieval farmer?” asked the sales engineer, opening and closing the pearl snaps on his shirt, sticking his hand thoughtfully down the back of his own waistband.

  Because interviewing at the e-book startup had been breezy and comfortable, I expected the same from the analytics company. No one had warned me that in San Francisco and Silicon Valley interviewing was effectively punitive, more like a hazing ritual than an airtight vetting system. A search-engine giant down in Mountain View was famous for its interview brainteasers, and while it had already denounced the practice, finding it useless as an indicator of future job performance, others insisted on enshrining it as tradition: learning from another company’s mistakes took on a new meaning when those mistakes had proved lucrative. Across the Bay Area, applicants were routinely asked questions like “How many square feet of pizza are eaten in the United States every year?” and “How many Ping-Pong balls fit in an airplane?” Some of them, meant to determine whether an interviewee was a culture fit, were dredged in middle-school kitsch. “If you were a superhero, what would your superhero strength be?” asked straight-faced human resources professionals. “When you walk into a room, what’s your theme song?” That afternoon, mine was a dirge.

  After a few hours, the technical cofounder entered the conference room, looking confidently unprepared. He noted, with an apology, that he hadn’t done many interviews before and didn’t have any questions to ask. Still, he said, the office manager had slated an hour for our conversation.

  This seemed okay: I figured we would talk about the company, I would ask routine follow-up questions, and they would finally let me out, like an elementary-school student, and the city would absorb me and my humiliation. Then the technical cofounder told me that his girlfriend was applying to law school, and he’d been helping her prep. Instead of a conventional interview, he said, he was just going to have me take a section of the LSAT. I searched his baby face to see if he was kidding.

  “If it’s cool with you, I’m just going to hang out here and check my email,” he said, sliding the test across the table and opening a laptop. He set a timer on his phone.

  I finished early, ever the overachiever. I checked the test twice. I joked that it was the closest I’d ever come to applying to law school—my mother would be so proud. The technical cofounder shot me a thin smile, slipped the papers under his computer, and left the room.

  I sat in his wake, wondering what I was waiting for. There was not a doubt in my mind that I would not get the job. Not only had I surely demonstrated that I was unemployable, but I felt certain I’d been a vivid caricature of the dotty, linty liberal arts major—the antithesis of all that the tech industry stood for.

  Still, though the interviews had been inane, they only served to fuel me. Here was a character flaw on parade, my industry origin story: I had always responded well to negging.

  * * *

  I would wonder for years if the analytics startup offered me the job because the entire interview process had revealed a degree of obedience desirable in a customer support representative, and in an employee—if they knew I would ultimately be a pushover, loyal and easily controlled. Eventually, I learned that it was actually just because I had managed a perfect score on the LSAT section they had administered. This knowledge would make me feel simultaneously cocky and displaced, of superior intelligence and crushing foolishness. A part of me had hoped they’d seen something latent and unique, some potential. I was always overthinking things.

  The offer included medical and dental coverage, a four-thousand-dollar relocation stipend, and a starting salary of sixty-five thousand dollars a year. The manager informed me that the salary was above market and nonnegotiable. I couldn’t fathom being someone who made that much money, much less someone who would try to negotiate for more. With my skill set, or lack thereof, I couldn’t believe anyone wanted to pay me that much to do anything.

  The solutions manager did not mention equity, and I didn’t ask. I did not know that early access to equity was a reason people joined private companies at the startup stage—that it was the only way anyone other than VCs and founders got rich. I did not even know that equity was an option. The company’s in-house recruiter would eventually intervene, to recommend that I negotiate to include even a small stake. His rationale was simple: all the other guys had some. No one told me how much it was worth, or how big the pool was, and I did not know to ask.
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  High on the feeling of being professionally desirable, I told the solutions manager I would sleep on it.

  * * *

  The analytics startup gave me three weeks. Back in Brooklyn, I invited friends over as I packed up the apartment. One evening, after a few drinks, a close friend asked whether I was sure I was making the right decision. I’d enjoyed working in publishing, she reminded me, idly popping bubble wrap between her fingers. Was it perhaps premature to throw in the towel? She promised not to judge if I decided, last minute, not to go. “Mobile analytics,” she said, trying on a pair of vintage spectator pumps that I had purchased in the midst of an identity crisis. “What is that? Do you care about it? And customer support—aren’t you worried it’ll be soul ruining?”

  I was worried about a lot of things: loneliness, failure, earthquakes. But I wasn’t too worried about my soul. There had always been two sides to my personality. One side was sensible and organized, good at math; appreciative of order, achievement, authority, rules. The other side did everything it could to undermine the first. I behaved as if the first side dominated, but it did not. I wished it did: practicality, I thought, was a safe hedge against failure. It seemed like an easier way to move through the world.

  Still, I had trouble admitting to my social group that I was moving across the country solely to work at a startup. It was embarrassing to articulate how excited I was to see what the fuss was about—it seemed, among my countercultural and creative friends, shrewd and cynical to be curious about business. I was selling out. In reality, I was not paying attention: those who understood our cultural moment saw that selling out—corporate positions, partnerships, sponsors—would become our generation’s premier aspiration, the best way to get paid.

  At the time, though, it was corny to be openly enthusiastic about technology or the internet. For the most part, my friends were late and reluctant adopters. They had accounts on the social network everyone hated, but only used them to RSVP to poetry readings and DIY shows they had no intention of attending. Some defiantly carried flip phones without internet access, preferring to call those of us with desk jobs whenever they were out and needed directions. No one owned an e-reader. As the tides turned digital, my milieu was grounding itself firmly in the embodied, tangible world.