Uncanny Valley

by Anna Wiener

  After surrendering my badge, I biked away from the office, wild with possibility. My backpack, light without a work laptop, flapped against my spine as I cruised up Market Street. I felt liberated, discharged. In the Panhandle, I passed a group of runners in matching startup T-shirts, trotting through the eucalyptus like a string of well-broke ponies, and I pitied them.

  That evening, Ian picked me up from home in a rental car, and we drove into Berkeley, snaking through the hills. We pulled over at a lookout and sat on a boulder, eating curried couscous and drinking cheap champagne. Across the bay, San Francisco flickered. Fog settled over the city, draping itself around the parks, the hills, the piers.

  All this time, and I could just leave. I could have left months ago. For nearly two years, I had been seduced by the confidence of young men. They made it look so simple, knowing what you wanted and getting it. I had been ready to believe in them, eager to organize my life around their principles. I had trusted them to tell me who I was, what mattered, how to live. I had trusted them to have a plan, and trusted that it was the best plan for me. I thought they knew something I did not know.

  I swam in relief. Watching the city, wrapped in Ian’s jacket, I did not see that I was in good company: an entire culture had been seduced. I understood my blind faith in ambitious, aggressive, arrogant young men from America’s soft suburbs as a personal pathology, but it wasn’t personal at all. It had become a global affliction.

  SCALE

  The open-source startup was an institution. People had been collaborating on free software for decades, long before the founders, four fresh-faced programmers in their twenties, revolutionized—and monetized—the scene. The startup, however, made the process faster, more reliable, social. The platform genuinely improved the lives of developers, who were predisposed to simple, elegant solutions designed by people who thought just like they did. The company had been profitable practically from the get-go, and was a paragon of product-market fit: catnip for venture capitalists. The founders decided to do things differently. There was no one to tell them no.

  The company was modeled on the free software community, with its subversive, countercultural, and deeply techno-utopian ethos. For years, in emulation of the tenets of open-source—transparency, collaboration, decentralization—the startup was flat. There was no hierarchy. There was no org chart. Employees had named their own compensation, determined their own priorities, and come to decisions by consensus. The founders did not believe in management, but in meritocracy: the best would naturally rise to the top.

  Everyone was encouraged to work how, where, and when they worked best—whether that meant three in the morning in the San Francisco office, referred to as HQ, or from inside a hammock on Oahu. They were invited to bring their whole selves into work, and reminded to take their whole selves on vacation. Vacation, which was unlimited, was not tracked. Business hours did not exist. Half the workforce was remote, and digital nomadism was considered banal.

  The company was obsessed with developers, and the feeling was mutual. Users displayed a level of brand loyalty that bordered on fanaticism. They tattooed the mascot onto their bodies and sent photos to Support, the skin raw and red, the ink still fresh. The web shop sold enough swag—branded clothing, stickers, barware, toys, infant onesies—that it could have been an independent business. Tour groups from around the world cruised through the office, taking selfies behind the Resolute desk and at the base of a six-foot statue in the lobby of the octopus-cat, cast in bronze and styled as The Thinker.

  Some employees were well-known in the open-source community, as high-profile maintainers of popular repositories or authors of programming languages. Others leveraged the startup for personal acclaim, blogging and branding their way to minor celebrity. They traveled the world as self-appointed corporate evangelists, hopping continents on the infinite conference circuit. They talked programming frameworks in Tokyo, design thinking in London, the future of work in Berlin. They spoke with the authority of tenured professors to audiences of eager developers, designers, and entrepreneurs, seas of men yoked with laminated day passes. They gave inspirational talks about the toxicity of meetings and waxed poetic about the transcendence of collaboration. They parlayed their personal experiences into universal truths. When they dropped by San Francisco, they walked around SoMa wearing the employee hoodie, acting like people were going to recognize them. Sometimes, people did.

  * * *

  I spent my first week on the job lurking, reading internal message boards and paging through chat room back-scroll. Despite the opulence of HQ, the buildout of which was rumored to have cost ten million dollars, the true headquarters of a remote-first company was the cloud. To ensure that all employees were on equal footing regardless of geography, the majority of business was conducted in text. This was primarily done using a private version of the open-source platform, as if the company itself were a codebase. People obsessively documented their work, meetings, and decision-making processes. All internal communications and projects were visible across the organization. Due to the nature of the product, every version of every file was preserved. The entire company could practically be reverse engineered.

  There were only two hundred employees, but the startup had, in a sense, built a private internet community. People referred to each other by their platform handles, both online and in person. Even the CEO signed off on emails and internal posts with his username. The corporate chat software lit up every few seconds with data, information, digital ephemera; it contained multitudes. There were channels for science fiction readers, comic book lovers, night owls, politics junkies. There was a channel for people to post photographs of dogs in the office, and a channel for people to post photographs of dogs they followed on social media. There were channels for barefoot-shoe enthusiasts, martial arts practitioners, recovering music majors. For people who loved karaoke, or basketball, or theme parks, or bland food, or sous vide machines. For people to talk about tiny homes. For knitters. Forty people belonged to a channel dedicated solely to the discussion of ergonomic computer keyboards.

  My coworkers were fanatics for emojis and deployed them liberally, as a substitute for language and a lever for passive aggression. A tiny whale, a tiny ice-cream cone, a tiny, steaming pile of shit. A tiny custom octopus-cat; a tiny photo of the CEO’s face. I was embarrassed by the thought of using my laptop in public spaces—my work looked like a video game for children.

  The archive of institutional knowledge, however, was fascinating. Absent any formal onboarding program, I made up my own. I read chat history from the period when the gender discrimination accusations were first made public; transcripts from all-hands meetings addressing the scandal; discussion in the Human Resources repository. I saw how my coworkers had reacted in real time, and who had been quick to throw the first woman in Engineering under the bus. Reading back-scroll made me feel like a creep, but it was a useful research project, a means of discovering whom to avoid and whom to trust.

  * * *

  My second week, I flew to Chicago to participate in a hack house. Hack houses were a routine practice across the company: every few months, teammates would convene in a city of their choice—Austin, Athens, Toronto, Tokyo—and spend a few days catching up, planning, and drinking. My new coworkers, digital assimilationists if not digital natives, referred to this as getting together in meatspace.

  The company had rented a mansion in the Gold Coast neighborhood, a sprawling Art Moderne villa that once belonged to a shoe heiress but had since been renovated and decorated with a garish minimalism that screamed porn set: geometric furniture, zebra rugs, white baby grand, and a full-sized stuffed steer. In my room, an en-suite bath was separated from the bed by half a wall of glass brick.

  The first night, I pushed my duffel bag against the bedroom door, which did not lock. Sometime before dawn, I awoke to the sounds of a technical support engineer, a gentle aviophobe who had taken an eighteen-hour train from Colorado, shuffling into the buil
ding and crashing in the room across the hall. I emerged the next morning to find his door open; he lay facedown on the bed, limbs spread, snoring.

  The Support team spent the daytime hours sprawled out on deep leather couches in the living room, talking about ordering takeout and making jokes in the chat channel while clearing the queue. In the evenings, the group monopolized top-rated New American restaurants for midwestern farm-to-table and traveled to black-box theaters for midwestern comedy. In the mornings, people woke up late and padded around the mansion in pajamas, frying bacon and responding to support tickets.

  While a weeklong sleepover would not have been my first choice for meeting new coworkers, I felt fortunate. My teammates were good-natured, funny, laid-back. Almost all of them were older than I was, and about half were women. A good number had previously been employed as librarians or archivists, and were drawn to the open-source startup for reasons similar to mine: the utopian promise of free, easily distributed, well-organized knowledge; a livable salary; really good benefits.

  My onboarding buddy, an earnest and thorough southerner who had previously worked at an education nonprofit, walked me through the internal ticketing software. The company’s engineers were picky, I noted: even the support queue integrated with the open-source platform.

  The ticketing software had been built by the first Supportocat, my onboarding buddy explained, and could be buggy. “Just ping him if anything breaks,” she said, and gave me the developer’s platform handle, a cute nickname that invoked a bear cub. What’s his name, I asked, and my onboarding buddy smiled. “That is his name,” she said. She leaned in confidentially. “He identifies as a tanuki, a Japanese racoon dog. Only the founders know his legal name.” Oh, I said, feeling very vanilla. “He’s at HQ sometimes,” she said. “You’ll know him by the tail.”

  On the second night, as we expensed nightcaps at a dive bar near the mansion, the mood turned, and the Supportocats started to talk shit. The company was struggling, my coworkers said—culturally, at least. The startup had enjoyed a prolonged awkward adolescence, and now it had to grow up. The founder who had left postscandal had been the lifeblood of the organization, and the CEO was well-intentioned but conflict averse. For the first time in the company’s history, people were threatening to quit.

  The employees were haunted by what had happened with the first woman engineer, my coworkers explained. Many had taken it personally. They’d been let down by people they considered to be family. They were heartbroken. They had been complicit, and hadn’t even known. They were terrified it would happen again.

  But also—it was complicated. “On the one hand, if we have a problem with sexism or sexual harassment, then that problem needs to be addressed,” a teammate told me. “On the other hand, this hurt everyone.” I asked what she meant, and she pushed her hair to the side. “I don’t know if the company will ever recover from this,” she said. “And, to put things bluntly, she wasn’t the only one with equity.”

  * * *

  Back in the office, there was a lot of chatter about a group of internet trolls who had mounted a harassment campaign against women in gaming. The trolls had flooded social networks, spouting racist, misogynistic, and reactionary rhetoric. They railed against feminists, activists, and those whom they dubbed, pejoratively, social justice warriors. They had been banned from nearly every other platform, and responded by citing the First Amendment and crying censorship. This caught the attention of some right-wing commentators and white supremacists, who offered endorsement and solidarity.

  On the open-source platform, the trolls maintained a repository of resources and information on women they were targeting—photos, addresses, personal information—and outlined strategies for stalking, harassment, and media pressure. The accounts contributing to the repository were mostly sock puppets, tied to burner emails and using an overlay network to obscure IP addresses. The people behind them were unidentifiable and impossible to trace.

  My coworkers debated how seriously to take the campaign. They were used to seeing social media weaponized in this way, they told me: trolls and shitposters existed on every platform, and were best flagged as spammers or ignored.

  “If you spend five minutes in gaming communities, you’ll see this sort of thing,” a teammate said. I hadn’t played a video game since I was a kid; I didn’t know there were communities. “They’re just a bunch of dudes in their parents’ basements,” he said. “They’ll move on.” Still, he admitted, looking at the repository of email templates and phone call scripts, it was unusual to see them so organized.

  The company did not have a formal team to handle these sorts of situations. An ad hoc collection of executives, support representatives, lawyers, and rubberneckers had formed a casual decision-making chat room called Hazmat, to deal with occasional controversies and platform flare-ups. After weeks of internal discussion, inaction, and complaints from the community, the Hazmat group disabled the repository. Immediately, employees were mobbed on social media. The Support inbox was flooded with death threats.

  I showed one of the engineers a particularly hostile message that had come into the queue. We looked up the email address in our admin tool, and found the associated account. The user profile had an avatar of a man with a thin mustache and wild eyes. “This is who you’re worried about?” the engineer asked. “Come on. You know who these people are. Dakimakura pillows, holes front and back. You’ll be fine. His mom’s not going to drive him to a murder.”

  The engineer rolled back to his desk, and I opened a new tab and searched dakimakura pillows. The world was vast and unknowable, I thought, flipping through product photographs. I felt very innocent and naïve.

  The people behind the sock-puppet accounts were just assholes, my coworkers said, dropping animated GIFs of eyerolling celebrities into the chat room. They were immature or bored, probably students: the company always saw an uptick in abuse reports during school vacations and over long weekends. Just a bunch of bad actors, they reassured me, atypical for the platform—not worth any more time, not worth our engagement.

  As an onboarding gift, the open-source startup gave all employees a step-count wristband: fit workers were happy workers, and probably cheaper to insure. I wore the wristband for a week, tracking my steps and calibrating my caloric intake, until I realized I was on the brink of an eating disorder.

  The ecosystem’s fetish for optimization culture and productivity hacking—distraction blockers, task timers, hermit mode, batch emailing, timeboxing—had expanded into biohacking. On the internet and in San Francisco’s finer coffee shops, systems thinkers swapped notes about their stacks and dosages. They optimized their sleep cycles with red light and binaural beats. They bought butter-laced cold brew, shot up their thighs with testosterone, and purchased haptic-feedback wristbands to self-administer 150-volt electric shocks.

  The body was a platform, the biohackers argued: if an upgrade was available for their laptop’s operating system, they would download it posthaste, without question. The same was true of their human organisms. New companies sold nootropics, unregulated cognitive-enhancement drugs claiming to unlock next-level thinking, to those striving for peak performance.

  I wanted to be above it, but I wasn’t above it. Too curious; too wistful for my college roommate’s ADHD medication. I ordered capsules of nootropics from a startup claiming to be manufacturing Human 2.0. The capsules weren’t approved by the FDA, but the startup was funded by the same investors who paid my salary. I took them in anticipation of high productivity, but my thinking remained locked, maxing out at the usual level.

  “I don’t like this new phase,” Ian said, inspecting the nootropics package. The capsules rattled in their glass jar, branded with a lightning bolt. “L-theanine? This is like what you get from a homeopath, just with flat design.” He declined my offer of a mocha-flavored caffeine gummy.

  There was something a little bit sad about body optimization, I thought, after accidentally spending an afternoon on noot
ropics in the bathroom with my eyelids taped, watching makeup tutorials and attempting to perfect a dramatic cat-eye. The goal was productivity, not pleasure. And to what end—whom did it serve? Perhaps gunning for high output in one’s twenties was a way to compress the peak-of-life productive years, tee up an early retirement with a still-youthful body, but it seemed brazen to play God with time.

  It seemed more likely that biohacking was just another mode of self-help, like business blogging. Tech culture provided endless outlets for men to pursue activities coded as female—including, apparently, body manipulation. I could see how tracking personal metrics offered a sense of progress and momentum, measurable self-betterment. Leaderboards and fitness apps encouraged community through competition. Quantification was a vector of control.

  Self-improvement appealed to me, too. I could stand to exercise more often, and be more mindful of salt. I wanted to be more open and thoughtful, more attentive and available to family, friends, Ian. I wanted to stop hiding discomfort, sadness, and anger behind humor. I wanted a therapist to laugh at my jokes and tell me I was well-adjusted. I wanted to better understand my own desires, what I wanted; to find a purpose. But nonmedical monitoring of heart rate variability, sleep latency, glucose levels, ketones—none of this was self-knowledge. It was just metadata.

  * * *

  Going into work wasn’t mandatory, but for a while I did it anyway. It was a pleasure to spend time at HQ, in the same way it would be a pleasure to kill a few hours in the lobby of a boutique hotel. There were vending machines stocked with new keyboards, headphones, cables, and cords, all of which tumbled down, free, with the tap of an employee badge. The elevators were never broken. An engineer was rumored to have lived in the office for a while, sleeping in a lounge area atop an indoor shipping container—a visual pun on shipping code—until he was discovered, by the security team, bringing home a date.