Uncanny Valley

by Anna Wiener

  As employees filtered past, the energy shifted. I was reminded of the gulf between us: Patrick was running a company, and I processed copyright takedowns and held users’ hands through account lockouts. I’d trolled him on the internet, and he’d taken the time to buy me lunch. He was the picture of grace, and I was lowly, unfocused, a rando with no goals. I wondered what kind of boss he was.

  We shook hands again, as if at the end of a job interview, and agreed to be in touch. It seemed safe to assume I would never see him again. Still, I had so many questions, so many things I wanted to talk to him about. A prison abolitionist who knew ancient Greek did not fit neatly into the archetype of a tech founder. I biked uphill toward my apartment, past tent encampments and antique streetcars, against the fog.

  * * *

  The message-board commentariat argued about whether it was more rewarding to work hard or work smart. They quantified qualitative things in amazing ways. Simple math, posted a data scientist at a company I’d never heard of. Monday to Friday is 71% of the week. The job won’t get done with 71% effort. I read the men’s disagreements while lying naked in bed with my work-issued laptop, keeping one eye on the queue.

  People argued about whether burnout was real, but also about burnout’s economic rewards. They shared links to pop-science articles about the creative potential of procrastination. They admired China’s “996” work schedule: 9:00 a.m. to 9:00 p.m., six days a week. They considered the value of seeing their young children; certain formative years were more important to be around for than others, some said.

  The men debated the role of equity in the ecosystem, the incentives for making fuck-you money. It’s about independence, one of the men wrote. It’s about the freedom to take a personal risk. When I thought risk, I didn’t think about money, mine or anyone else’s. Risk was white jeans on my period, coffee on an airplane, hitchhiking, the pull-out method. But the men weren’t talking to, or about, me; they never were. It’s about leverage, posted a self-described top performer. It lets me grab our executives and board by the balls.

  Fuck-you money: it was a catchphrase, a motivation, a lifestyle. According to people on the internet taking a dip in the shallow pools of libertarianism, it was pure American freedom. It was a state of mind, argued a startup founder on his company blog—it was an attitude. Money: it wasn’t about the money. After a certain threshold, at least, it really wasn’t.

  A venture capitalist who would later be the subject of sexual harassment allegations helpfully chimed in to say that fuck-you money went much further in Thailand. By his metrics, a million dollars in Southeast Asia would be more than enough. Maybe even a few hundred thou, he wrote.

  Side arguments broke out about whether financial gain—the prospect of fuck-you money, that luscious carrot on the stick—was the right incentive for startup employees. I disagree with the premise, wrote a man whose handle invoked an imaginary animal. Are you implying that the only reason to work is for the money?

  * * *

  I did see Patrick again. We met for dinner at a restaurant on the far side of Bernal Hill, an outgrowth of another internet argument; then dinner in the Mission, an outgrowth of an unfinished conversation; then dinner in the Outer Sunset, at which point we had established a friendship that felt nearly familial in its combativeness and ease.

  Patrick complicated my expectations for the entrepreneurial class. He did not exhibit much desire to strut across conference stages or digitally thought-lead; it was impossible to imagine him bullying employees or doing shots. Friends who met him often assumed he was a graduate student. We had little in common, in terms of our extracurricular interests—one evening, walking past a DIY venue, he looked at the art-punk kids standing outside and said, dryly, “So this is where the youth go for the bippity boppity”—but I found this very relaxing. No pretenses; no posturing. He wore thin-framed glasses that improved his vision without signaling any subcultural affiliation, and was wildly smart. I always wanted to know his opinion.

  We mostly spent time together in upscale New American restaurants, where Patrick had no trouble making same-day reservations. The restaurants were full of natural fibers and acacia accents, unobtrusive flora and barre-body waitresses in linen shifts; couples in their thirties and forties, the women wearing sturdy ankle boots and understated engagement rings, the men dressed, typically, to traverse a glacier. There was always at least one table of startup employees out for a team-building dinner, tucked somewhere they would not overly influence the ambience.

  San Francisco was going through a culinary renaissance, a competitive effort to capture the attention of young money. Chefs were not competing with each other so much as against the apathy inspired by upscale office cafeterias, fast casual, and delivery apps. To differentiate themselves, they spun the dial all the way up, treating fried anchovies like luxury items and meting out slices of sourdough bread like manna from heaven. The food was demented: cheese courses hidden beneath table candles and revealed, perfectly softened, at the end of the meal; whole quail baked into loaves of bread. It was high-intensity, sensory overload: smoked corn-husk chawanmushi, pickled French fries, green beans and cherries enrobed in burrata. Food that the chef mandated be eaten by hand. Food that was social media famous. Food that wanted to be.

  After a string of starched-linen dinners, the friendship started to feel a little formal. We attempted alternate activities: a hike at six in the morning, a power breakfast at seven. Finally, I realized dinner was just the way Patrick hung out; it was the only consistent block of personal time in his schedule.

  It was easy to interrogate everyone’s relationship to power and status except for my own. I did not really care that Patrick ran a company, but I knew that other people did. I was flattered that he wanted to be friends with me, and surprised that he put in the time and the work. This brought out a side of my personality I wasn’t proud of. I let him off the hook for things I would have called out in other friends: he was not a reliable communicator, he could be curt, he would solicit time-consuming input on various projects and forget to acknowledge the feedback. When he interviewed a close friend of mine for a job, only to go dark, I felt ashamed, and annoyed, and said nothing. But Patrick had calls to take, meetings to run, time zones to juggle, flights to catch, teams to manage, executives to hire, investors to please. His time was no more valuable than my time, his life no more important than anyone else’s life—except, by the terms governing the ecosystem, it was.

  * * *

  Walking through the Mission to meet Ian for dinner, I bumped into one of the support engineers from the analytics startup. “My army buddy,” he said, embracing me. He smelled like mango vape. I laughed, not realizing he was serious. “We’ve been in the shit together,” he continued. “I’ve held you in my arms while you cried your heart out, like the world was ending.” I adored him, but I did not remember crying into anyone’s arms—I had always been careful to cry alone, in the bathroom. I was certain this had not happened. I said so, and he shrugged. “Why would you remember it?” he asked. “It was a totally normal thing to happen in that environment.” I did not tell him that I had recently considered returning.

  We stood on the street, hands in our pockets, stepping out of the way for commuters and shoppers and a woman pushing a cart of personal possessions. The support engineer told me that he had left the company. The CTO, the wide-eyed, self-taught genius, had left, too.

  “I heard he sold a bunch of his stock back,” the support engineer continued. “Instant multimillionaire. No question.” There was a question, actually: we had no way of knowing whether he’d sold his stock back and made millions. Still, the story seemed plausible enough. It was thrilling to even consider that the dream had come alive for someone we knew, of whom we were fond. Though the CTO had had a managerial title, I had always considered him one of us.

  What do you think he wants to do next? I asked. I wondered if the CTO might be working on his own games. I was excited for him.

 
The support engineer thought about it a moment. “Good question,” he said. “I don’t think he wants to do anything.”

  I joined a new team, Terms of Service, created to deal with the overflow of semi-legal concerns and complaints about objectionable material that choked the support queue. The open-source platform was, at its core, a file-hosting service: users could upload text, images, animations, and documents. While the interface could be intimidating to people who were not programmers, the public product was still used and abused like any other social technology that relied on free, user-generated content.

  The Terms of Service team handled copyright takedowns, trademark infringement, and spam; user deaths and COPPA violations. We took over the work of the Hazmat group, evaluating threats of violence, cryptocurrency scams, phishing sites, suicide notes, and conspiracy theories. We puzzled over reports of Great Firewall circumvention. We ran emails claiming to be from the Russian government through translation software and passed them to Legal with spinning question-mark emojis. We sifted through reports of harassment, revenge porn, child porn, and terrorist content. We pinged our more technical coworkers to examine malware and purportedly malicious scripts.

  We became reluctant content moderators, and realized we needed content policies. My teammates were thoughtful and clever, opinionated but fair. Speaking for a platform, however, was nearly impossible, and none of us were particularly well qualified to do it. We wanted to tread lightly: core participants in the open-source software community were sensitive to corporate oversight, and we didn’t want to undercut anyone’s techno-utopianism by becoming an overreaching arm of the company-state.

  We wanted to be on the side of human rights, free speech and free expression, creativity and equality. At the same time, it was an international platform, and who among us could have articulated a coherent stance on international human rights? We sat in our apartments tapping on laptops purchased from a consumer-hardware company that touted workplace tenets of diversity and liberalism but manufactured its products in exploitative Chinese factories using copper and cobalt mined in Congo by children. We were all from North America. We were all white, and in our twenties and thirties. These were not individual moral failings, but they didn’t help. We were aware we had blind spots. They were still blind spots.

  We struggled to draw the lines. We tried to distinguish between a political act and a political view; between praise of violent people and praise of violence; between commentary and intention. We tried to decipher trolls’ tactical irony. We made mistakes.

  Coming to decisions was, of course, as complex and nuanced and subject to interpretation as the content itself. Even pornography was a gray zone: nipples needed to be contextualized, but we weren’t trying to be puritanical. An artistic photograph of a woman breastfeeding was not the same as an avatar of an anime character spouting milk from physiologically untenable breasts. But what was art, anyway, and who were we to define it?

  Intent mattered, we reminded each other—repositories that contained assets for sex-education websites, for example, should be acceptable. At the same time, the platform was meant to be educational. We didn’t necessarily want people looking for package managers stumbling across folders of genitalia instead.

  I sometimes wondered whether the executive team knew that there was pornography or neo-Nazi drivel on the platform, or that well-intentioned employees working under Support, people who had been hired for intangible qualities like “good judgment” and “attention to detail,” were constantly bugging Legal to define—and enforce—what would be understood as the company’s position on free speech.

  Most of the company did not seem aware of how common it was for our tools to be abused. They did not even seem to know that our team existed. It wasn’t their fault—we were easy to miss. There were four of us for the platform’s nine million users.

  * * *

  The list of chat channels was growing: Latinx, Neurodiverse, 40+, Octoprentices, Octoqueer, NB, Blacktocats. The diversity and inclusion consultant had come on full-time, as VP of a new team called Social Impact, and with her guidance the startup was slowly becoming more diverse. Activists joined, as did some of the startup’s most vocal critics.

  One of these critics, Danilo, could have been a poster child for meritocracy—he was born to a single mother in Puerto Rico, raised in public housing, and had taught himself how to code as a kid—but he spoke openly about his contempt for Silicon Valley’s rugged-individualist narratives, and was fond of mocking venture capitalists and rabid techno-libertarians on social media. He clearly made some of our coworkers nervous.

  Danilo’s vision for technology was new to me. It relied on disruption, as was the fashion, but what it disrupted was Silicon Valley. The cost of participation in technology was plummeting, he liked to point out. As education, hardware, and access to tools got cheaper, more people would participate. The products and companies would diversify; the power structure would morph. “A whole new generation of technologists will do an end run around our whole system,” he told me, as we worked together one afternoon from HQ, sitting onstage in the empty event space. “We have this space with unprecedented influence and leverage for social change, and a whole generation coming up that was raised on broadband. That generation is going to come in and fuck it up.” Even venture capitalists would eventually be disrupted and rendered obsolete. I found this all very exciting—a way to reformat cynicism about the industry as optimism about the future.

  In late fall, the VP of Social Impact arranged for a visit from the secretary of Housing and Urban Development. The company had been working on an initiative of his, to bridge the digital divide by bringing high-speed internet, computers, and educational programs to people in low-income housing. I had spent a week in Washington, D.C., sitting in on meetings about the initiative, and had found it encouraging to hear elected officials—rather than the industry’s self-appointed leaders of borderless digital societies—talk about how technology could change the world.

  The day of the secretary’s visit, the office buzzed. The CEO posted to the internal message board, alerting us to the presence of actual Secret Service. Members of the Social Impact team looked anxious, electrified, as a phalanx of publicists and mixed-tier security toured the secretary through HQ. The actual Secret Service’s elegant suits and pins, in sober comparison to our Secret Service’s octopus-cat shirts, made me wince.

  Did they walk him through the Oval Office? I asked a coworker. She closed her eyes. “We are so fucking embarrassing,” she said.

  At the designated hour, everyone filed into the third-floor amphitheater. We came off a little careless and irreverent, I thought, surveying the loose T-shirts and scuffed-up shoes my colleagues and I were wearing. Various midlevel managers rushed around, instructing employees on where to sit. I hadn’t seen so many people in the office since our holiday party.

  Danilo gave a brief introduction. “The internet is an accelerant for growth and a dissolver of class walls,” he said. “It is a global classroom and community.” Out of the corner of my eye, I saw one of the company’s lawyers eating a miniature candy bar and looking peacefully stoned.

  “Most of all, it is the ticket to twenty-first-century prosperity,” he continued. “As a technologist, I feel a moral duty to help ensure its gifts reach all who need them.” I heard the rustle of polypropylene and the snap of a crispy peanut-butter core. The lawyer stared straight ahead, chewing.

  The secretary and the VP of Social Impact discussed the initiative. A quarter of United States households did not own a home computer, they noted; the digital literacy gap was also a gap in opportunity. The secretary, wearing a full suit and gleaming leather brogues, looked polished and hyperrealistic in the way that politicians tend to look. He looked out of place. I wondered what it felt like to lead a life of public service—climbing the ladder, accumulating credentials, walking the thinnest lines, probably owning a tuxedo—only to find himself catering to the growing power center of Silic
on Valley, with its baby tyrants, all the one-hit wonders who had dropped out of school and become their own bosses and thought they knew how the world worked, thought they knew how to fix everything. All the unicorn companies with in-house lobbyists poached from political consultancies, the billionaires who resisted regulation and expertise. Maybe it felt the same as catering to Wall Street, or the pharmaceutical industry, or Big Agriculture. Maybe it felt like envy: tech, after all, was a foil for some of the bureaucratic tedium that addled government. Anyone who had been to the DMV could make a case for disruption. Then again, I could only imagine the nightmare that would be a startup-run regulatory body.

  At the end of the presentations, our CEO, in low-riding jeans and a blazer, reemerged for closing remarks. He strode across the stage with an employee sweatshirt draped over his arm, just like the ones worn by our locally famous engineers. He and the secretary of HUD shook hands. As a token of thanks, the CEO said, he was proud to present the secretary with his very own personalized hoodie.

  * * *

  On the train to HQ one morning, scrolling through social media apps on my phone, an algorithm served up a photograph taken at the analytics startup’s holiday party. The photograph was of two former coworkers, both of them smiling broadly, their teeth as white as I remembered. “So grateful to be part of such an amazing team,” the caption read. The party had its own hashtag, and I tapped through.

  The hashtag unleashed a stream of photographs featuring people I’d never met—beautiful people, the kind of people who looked good in athleisure. They looked well rested. They looked relaxed and happy. They looked nothing like me.