Uncanny Valley

by Anna Wiener

  Not seriously, I lied.

  I had chosen to leave, I said, but I still felt pushed out of the club. It could be nice to overwrite my own feelings of failure, on my own terms: to prove to the CEO, and to myself, that I belonged. Ian squinted at me. “I don’t think your stubbornness about this will ever be rewarded,” he said. “If you want to write, write about something you care about, not about stuff like how to use funnels for user onboarding.”

  It could be a good chance to own something, I said, unconvincingly; I couldn’t imagine the CEO ever letting an employee own anything. I could build out a portfolio, I said. It could be interesting.

  We exchanged a meaningful look. “Not that interesting,” Ian said.

  * * *

  I went to New York. On previous trips home, when I was still working at the analytics startup, the city had felt fraught with paths not taken. All these past selves, marching around like they knew something; casting aspersions on my all-encompassing tech-centric identity; trying to convince me I had made a mistake. This time, I felt lighter. I reported into work from my childhood bedroom, making myself available between six in the morning and early afternoon. I saw college friends, and didn’t try to recruit anyone. I drank coffee with my mother until the coffee ran out or ran cold; visited my grandparents in apartments that hadn’t changed for decades. I tried to clear out the storage space in the basement, unearthing old bomber jackets with hand-sewn patches, undergraduate writing, a jar of peeled potatoes stockpiled fifteen years prior in preparation for Y2K. Banal activities, but they felt so good. I felt myself returning to myself.

  It was strange to be back, but with tech money. I invited friends to dinner at restaurants I knew about from my boss at the literary agency, opened bar tabs, took cabs home after midnight instead of waiting for the train. Killing time in an over air conditioned wine bar in the West Village one evening, sucking on Castelvetrano olives and feeling fancy, I thought about a conversation I’d once had with Noah, in which he had described joining the tech industry as both a personal defeat and a concession to his hometown’s new identity. Money, he said, gave him access to San Francisco’s growing network of private spaces, which had become most of the city. Money was a key.

  New York held my whole life, but the city I had grown up in no longer existed. There were some holdouts—the cat-smelling bookstore where I had worked during college breaks, certain cultural institutions—but the neighborhoods I had known as a child were now dotted with restaurants playing overdetermined playlists and boutiques trading on a branded locality that I found comical and alienating. The new version of the city was inscrutable, baffling. Who wanted this? Who was it for?

  In North Brooklyn, I asked a bookseller about the new buildings on the waterfront. The bookstore was full of oversized art books that were easy to imagine sitting on glass-top coffee tables in glass-walled apartments. I couldn’t find anything I wanted to read. Who lives there, I asked. The bookseller shrugged, and straightened a display of unlined notebooks. “Wall Street people, hedge fund types,” he said. “Tech bros.” Tech bros, I thought—here, too.

  The nature of cities was to change, I knew. I tried not to feel entitled: I was aware that my parents, who had moved to Brooklyn in the early 1980s, had once been the outsiders rewriting the borough, just as I had spent four years contributing to the erosion of Polish and Puerto Rican Greenpoint. I knew that I was doing the same thing out west, no matter how many times I tried to tell myself that it was temporary. Acceptance of complicity, on both coasts, was still a passive act. It ameliorated nothing.

  The city was beginning to look like a generic idea, perhaps sprung from the mind of a real estate developer, of what a wealthy metropolis should be. Developers could make condos out of anything. Young money ran amok. There were so many coworking spaces and upscale salad shops; so many anemic new buildings with narrow balconies. Walking through downtown Brooklyn, the force of time tumbling forward, I felt, for a moment, that I might viscerally understand some of the rage and grief I witnessed from longtime residents back in San Francisco.

  * * *

  Toward the end of the trip, I went with my friend Leah to see a performance by a musician and choreographer we both knew. The show was beautiful and strange, unsettling. Watching dancers roll gently across the floor of the black-box theater, I cried a little, wiping my nose on the program. I felt moved, buoyant, more alive, and desperately impressed with our friend—for making art in the face of a culture that hardly valued creative work, for building a life around it, for his grace and conviction. I glanced at Leah, a check on my passions; she held her chin in her hands, significantly more dignified but no less transfixed.

  The performance had a two-night run. It may have been video-recorded, but it felt like it was just for us. Afterward, the choreographer stood in the theater lobby, flushed and bashful, receiving bouquets wrapped in butcher paper. People in structurally inventive clothing lingered to synthesize over plastic cups of wine. We kissed the choreographer and gave our congratulations, then shuffled over to let in friends waiting on the periphery.

  As we left the theater in pursuit of a hamburger, I felt rising frustration and resentment. I was frustrated because I felt stuck, and I was resentful because I was stuck in an industry that was chipping away at so many things I cared about. I did not want to be an ingrate, but I had trouble seeing why writing support emails for a venture-funded startup should offer more economic stability and reward than creative work or civic contributions. None of this was new information—and it was not as if tech had disrupted a golden age of well-compensated artists—but I felt it fresh. I emitted this stream of consciousness at Leah, swearing to delete my ad-blockers and music apps, while she hailed us a cab.

  “Why not just leave, find something else you’re excited about?” she asked, as we rumbled across the Williamsburg Bridge, heading toward the restaurant where she worked.

  Money and health insurance, I said—and the lifestyle. I had never really considered myself someone with a lifestyle, but of course I was, and insofar as I was aware of one now, I liked it. The tech industry was making me a perfect consumer of the world it was creating. It wasn’t just about leisure, the easy access to nice food and private transportation and abundant personal entertainment. It was the work culture, too: what Silicon Valley got right, how it felt to be there. The energy of being surrounded by people who so easily articulated, and satisfied, their desires. The feeling that everything was just within reach.

  Was I trying too hard to make this mean something? I asked Leah. Was that just buying into the industry’s own narratives about itself? I tried to summarize the frantic, self-important work culture in Silicon Valley, how everyone was optimizing their bodies for longer lives, which could then be spent productively; how it was frowned upon to acknowledge that a tech job was a transaction rather than a noble mission or a seat on a rocket ship. In this respect, it was not unlike book publishing: talking about doing work for money felt like screaming the safe word. While perhaps not unique to tech—it may even have been endemic to a generation—the expectation was overbearing.

  Why did it feel so taboo, I asked, to approach work the way most people did, as a trade of my time and labor for money? Why did we have to pretend it was all so fun?

  Leah nodded, curls bobbing. “That’s real,” she said. “But I wonder if you’re forcing things. Your job can be in service of the rest of your life.” She reached out to squeeze my wrist, then leaned her head against the window. “You’re allowed to enjoy your life,” she said. The city streaked past, the bridge cables flickering like a delay, or a glitch.

  * * *

  At the airport a week later, waiting to board my return flight, a man standing at the front of the line caught my eye. He looked familiar, in a distant-relative, someone’s-husband sort of way. I shuffled closer, overstuffed camping backpack digging into my shoulders, and realized it was the CEO of the e-book startup. Standing beside him were the CPO and CTO. Even in the terminal�
�s fluorescence, all three looked trim and energized. Their carry-on bags were modest in size and immaculate. I had wolfed a turkey sandwich in the food court, and was aware that I had a slight mustard odor. I already felt disarmed by their good attitudes.

  The founders and I greeted each other warmly. I was a little surprised that they remembered me—over two years had passed, a decade in startup time. I was ancient history. The e-book startup had grown, raising an additional seventeen million dollars and expanding to include women and an editorial staff. The company even had an online literary magazine, which I tried not to take personally. I wondered if the founders had actually liked me. I wondered if they were seated in business class.

  “Where are you these days?” asked the CEO, with characteristic enthusiasm. I felt bad that I hadn’t followed up, and worse that I couldn’t tell him I had launched my own company or at least become a junior analyst at a venture firm. I said I was working at the open-source startup, and the founders seemed to approve; then I added that I was doing customer support, and watched their faces shift to a polite neutral. I’ve also started writing book reviews, I appended meekly. I had written a handful of reviews for a magazine my mother once described fondly as “the ideological left talking to itself” but that was now being driven into the ground by its new owner, a billionaire cofounder of the social network everyone hated. I knew the founders would be familiar with the billionaire owner; it seemed less likely they read the magazine. They nodded supportively.

  The men were vague about their plans for the Bay Area. Just some meetings, they said. I asked if they might have free time, and they clarified that it would be a quick visit. Right, I thought, business. What did I think we were going to do, go on another field trip? I was delusional. After a few minutes I said goodbye, and returned to my boarding group at the back of the line.

  A few months later, reading the heavily moderated message board, I better understood their vagueness: the e-book startup was closing the service. They had probably been in San Francisco to meet with their investors, wind things down. The company had been purchased by the search-engine giant, in what was rumored to be an eight-figure acquihire.

  * * *

  Back in San Francisco, I felt acutely aware of the city’s beauty, and of the inbound aesthetic shift. Half the knowledge workers I encountered had the same thin cashmere sweaters I did, and the same lightweight eyeglasses. Some of us had the same skin tints, from the same foundation. We complained of the same back problems, induced by the same memory-foam mattresses. In apartments decorated with the same furniture and painted the same shades of security-deposit white, we placed the same ceramic planters holding the same low-maintenance plants.

  Efficiency, the central value of software, was the consumer innovation of a generation. Silicon Valley might have promoted a style of individualism, but scale bred homogeneity. Venture-funded, online-only, direct-to-consumer retailers had hired chatty copywriters to speak to the affluent and overextended, and we appeared to be listening.

  The direct-to-consumer companies sold cotton T-shirts, toothbrushes, rubber trees, rash cream, skin cream, leather bags, meal replacements, luggage, linens, contact lenses, cookies, hair dye, athleisure, wristwatches, vitamins. On any given night in America, exhausted parents and New Year’s–resolution cooks were unpacking identical cardboard boxes shipped by meal-prep startups, disposing of identical piles of plastic packaging, and sitting down to identical dishes. Homogeneity was a small price to pay for the erasure of decision fatigue. It liberated our minds to pursue other endeavors, like work.

  Persuaded by the testimonials of two infrastructure engineers, overnight converts to orthotic sensibility, I ordered a pair of unembellished, monochrome merino-wool sneakers. I’d been noticing them on people in coffee shops and in line at no-cash food trucks, and in advertisements on my social media feeds. The sneakers looked like a child’s drawing of a shoe, a shoe distilled to its essence, but they were incredibly comfortable. I didn’t know if wearing them outside was an act of radical self-respect, or the exact opposite. They sat unworn by the apartment door, a monument to the end of sensuousness.

  Wasting time on the microblogging platform one morning, I fell into an argument with the founder of a startup who was making the case, to his seventy thousand followers, that books should be shorter and more efficient. It’s unfortunate that the world doesn’t reward conciseness more, he posted. Making books shorter would effectively increase the rate at which we can learn. Or, put another way, the broken incentives today are probably *halving* (or more) the rate at which you can learn. Be mad!

  I was mad. Mad that tech entrepreneurs like him seemed constitutionally unable to resist cannibalizing music, books, subcultures—whatever made life interesting. Reading wasn’t about mainlining information. The tech industry’s efficiency fetish was so dreary. Don’t encourage your claque, I thought. I took a screenshot of his post, and shared it with a little editorialization: Tech needs to stop trying to ruin everything I love, I sniped.

  My social media use usually tapped out at making jokes about books with a small group of friends, but the post began to circulate, and I began to panic. I wasn’t used to having an audience, and didn’t want one. It was preferable to lurk, ideal to be invisible. Also: didn’t I have anything better to do?

  I clicked through to the founder’s profile page. Optimist, fallibilist, read the account bio. CEO. The avatar was a professional headshot. His shoulders curved forward, clavicle protruding from the neck of a loose cotton T-shirt. The only other people I knew with professional photographs were aspiring actors who needed to audition for Hollywood films and antacid commercials, but he could have been cast: he was handsome, and had an air of self-possession. I could practically hear the photographer advising him to soften his eyes, to look focused but compassionate.

  Optimist in which way, I wondered. In the Candide way, the Jeffersonian way, or the Oscar Wilde way? I looked up Oscar Wilde optimism quote—“The basis of optimism is sheer terror”—and felt affirmed. I looked up “fallibilist” and found myself on a website about philosophy and medieval mathematical truths.

  When I searched the optimistic, fallibilistic CEO’s name, the search engine autofilled the appendages “girlfriend” and “net worth.” On social media, he posted earnestly about biographies of physicists and tech luminaries, and shared sweeping landscape photographs from trail runs and bike rides. He was younger than I was, but that was starting to seem like a given.

  As I was about to close out the search results, I saw a photograph of him as a teenager, dressed in a Catholic school uniform. His tie was tucked into his sweater, and he brandished a trophy from a prestigious science competition, a look of sheepish pride stretched across his face. He could have been any one of my friends from high school. It was impossible not to smile back at my laptop.

  I followed up, though the CEO had not responded, and added an apology, tagging him into the conversation I was having with myself. He quickly wrote back, and the disagreement migrated over to email, where he invited me for lunch.

  A few weeks later, I biked from work to his company’s office in the Mission. With teenage-like impudence and a vain savior complex—I had the ear of a social media influencer, I thought, and not only would I bend it, I would introduce it to art—I had brought along a small stack of books to give him, all of which espoused different versions of my own aesthetic or political inclinations. They also pandered to what I believed were his interests, in that they were short. At the top of the pile was a copy of Are Prisons Obsolete?, about which I was especially smug. I cruised through SoMa, congratulating myself on speaking truth to power, sticking it to the Man.

  The CEO met me at reception, and introduced himself as Patrick. He was skinny and freckled, with glacier eyes and a mop of curls—much less intimidating than the headshot, much more polite than the Man. He wore running sneakers and a lightweight athletic jacket. We walked to a café and sat on a bench outside, eating lentil salad and rehas
hing our conversation from the microblogging platform.

  To my surprise, I liked him. He was wry, and very charming. He spoke in complete, eloquent paragraphs. We compared notes on working at pickax companies and the books we were reading, and swapped childhood stories. He told me about studying ancient Greek with a monk in the countryside where he grew up, and the drifting, lost time he’d spent between his first startup and the current one. Later, I would hear him repeat these same anecdotes in media interviews and feel a little cheated: I wasn’t used to people with well-worn origin stories. Then again, I wasn’t used to being around people who were asked for them.

  I told Patrick about my book reviewing, and he asked whether it was something I wanted to do full-time. Oh, I said—that’s not a job. I made a joke about the golden handcuffs of startup health insurance, and he asked if health insurance was the one thing keeping me from quitting my job and pursuing my goals. No, I said, worried that he might offer to pay for it. The one thing keeping me from pursuing my goals was that I didn’t know what, exactly, my goals were.

  “Ah,” he said, pushing a lentil around the biodegradable container. There were qualities I wanted for my professional life, I continued, quickly. I wanted work to be intellectually engaging, and I wanted to do it alongside smart, curious people. I wanted long-term projects. I wanted it to matter. Patrick listened patiently as I processed fourteen years of liberal arts education and aspirational upper-middle-class messaging in real time. Then we sat quietly for a moment, gazing into the street, my directionlessness like a third wheel.

  We walked back to my bike. As we stood by the door to his office, I handed Patrick Are Prisons Obsolete?, and he grew animated. He was fascinated with the American prison-industrial complex, he said. Incarceration in the United States was one of the greatest shames of the modern era. History would indict us, he said, and history would be right. Knowing he had dropped out of college, I offered to share the syllabus from a seminar I’d taken on the carceral state. He politely sipped the dregs of his iced tea.