Uncanny Valley

by Anna Wiener

Depending on whom you ask, it was either the apex, the inflection point, or the beginning of the end for Silicon Valley’s startup scene—what cynics called a bubble, optimists called the future, and my future coworkers, high on the fumes of world-historical potential, breathlessly called the ecosystem. A social network everyone said they hated but no one could stop logging in to went public at a valuation of one-hundred-odd billion dollars, its grinning founder ringing the opening bell over video chat, a death knell for affordable rent in San Francisco. Two hundred million people signed on to a microblogging platform that helped them feel close to celebrities and other strangers they’d loathe in real life. Artificial intelligence and virtual reality were coming into vogue, again. Self-driving cars were considered inevitable. Everything was moving to mobile. Everything was up in the cloud. The cloud was an unmarked data center in the middle of Texas or Cork or Bavaria, but nobody cared. Everyone trusted it anyway.

It was a year of new optimism: the optimism of no hurdles, no limits, no bad ideas. The optimism of capital, power, and opportunity. Wherever money changed hands, enterprising technologists and MBAs were bound to follow. The word “disruption” proliferated, and everything was ripe for or vulnerable to it: sheet music, tuxedo rentals, home cooking, home buying, wedding planning, banking, shaving, credit lines, dry cleaning, the rhythm method. A website that allowed people to rent out their unused driveways raised four million dollars from elite firms on Sand Hill Road. A website taking on the kennel market—a pet-sitting and dog-walking app that disrupted neighborhood twelve-year-olds—raised ten million. An app for coupon-clipping enabled an untold number of bored and curious urbanites to pay for services they never knew they needed, and for a while people were mainlining antiwrinkle toxins, taking trapeze lessons, and bleaching their assholes, just because they could do it at a discount.

The only way to have a successful and sustainable career in the publishing industry, it seemed, was to inherit money, marry rich, or wait for peers to defect or die.

My desires were generic. I wanted to find my place in the world, and be independent, useful, and good. I wanted to make money, because I wanted to feel affirmed, confident, and valued. I wanted to be taken seriously. Mostly, I didn’t want anyone to worry about me.

The CEO did not acknowledge that the reason millennials might be interested in experiences—like the experience of renting things they could never own—was related to student loan debt, or the recession, or the plummeting market value of cultural products in an age of digital distribution. There were no crises in this vision of the future. There were only opportunities.

began to wonder why it was, exactly, that they had hired me. I had been operating under the vain premise that it was because I knew something about books: I could be a bridge between the old and new guards. I had fancied myself a translator; I had fancied myself essential. Later, once I better understood the industry-wide interest in promoting women in tech—if not up the ranks, then at least in corporate marketing materials—I would allow myself to consider that perhaps I was more important to the aesthetic than critical to the business.

What I also did not understand at the time was that the founders had all hoped I would make my own job, without deliberate instruction. The mark of a hustler, a true entrepreneurial spirit, was creating the job that you wanted and making it look indispensable, even if it was institutionally unnecessary.

“She’s too interested in learning, not doing,” the CEO typed once into the company chat room. This was an accident—he meant it only for the other two cofounders. We huddled in the conference room and he apologized sincerely, while I looped the words over and over in my head. I had always been interested in learning, and I had always been rewarded for it; learning was what I did best. I wasn’t used to having the sort of professional license and latitude that the founders were given. I lacked their confidence, their entitlement. I did not know about startup maxims to experiment and “own” things. I had never heard the common tech incantation Ask forgiveness, not permission.

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.

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.

He would lambaste the weak local sports teams, the abundance of bicyclists, the fog. Like a woman who is constantly PMSing, a twenty-three-year-old founder of a crowdfunding platform wrote about the climate. The extension of casual misogyny to weather was creative, but the digital ambassadors didn’t seem to like actual women, either: they whined that the women in San Francisco were fives, not tens, and whined that there weren’t enough of them.

This concentration of public pain was new to me, unsettling. I had never seen such a shameful juxtaposition of blatant suffering and affluent idealism. It was a well-publicized disparity, but one I had underestimated. As a New Yorker, I had thought I was prepared. I thought I’d seen it all. I felt humbled and naïve—and guilty, all the time.

Research showed little correlation between productivity and extended working hours, but the tech industry thrived on the idea of its own exceptionalism; the data did not apply to us.

When the engineer went to the bathroom, I looked up his account on the photo-sharing app and scrolled through: fog at Lands End, fog on Muir Beach, crashing waves, copper hills. The Golden Gate Bridge at daybreak, at sunset, at night. Half the photographs featured either his bicycle or a strip of empty road. They were, I had to admit, very high resolution. It seemed stressful to me, cultivating a public image, or a personal aesthetic—like the sort of mind-set that could lead a person to worry during sex about whether the lighting was sufficiently cinematic. I knew I didn’t fit into the engineer’s meticulously curated life. I knew we’d never hang out again, though I also knew that I would try.

Being the only woman on a nontechnical team, providing customer support to software developers, was like immersion therapy for internalized misogyny. I liked men—I had a brother. I had a boyfriend. But men were everywhere: the customers, my teammates, my boss, his boss. I was always fixing things for them, tiptoeing around their vanities, cheering them up. Affirming, dodging, confiding, collaborating. Advocating for their career advancement; ordering them pizza. My job had placed me, a self-identified feminist, in a position of ceaseless, professionalized deference to the male ego.

I often wondered what work was like for our communications director, who was in her mid-thirties and had come through the investors. She was vastly more experienced than anyone else at the company, and far too professional to gossip or complain. She left the office every day at 5:00 to pick up her kids, and I suspected she was penalized for this: marketing and communications did not grow with the rest of the startup. There was no one else on the team. The CEO kept a drawing of himself, made by one of her children, pinned to a corkboard next to his workstation.

I was the feminist killjoy. I did not pick my battles. I died on every available hill. I asked my coworkers to stop using words like “bitch” in the company chat room. I bitched about being one of six women at a company of fifty. I wondered aloud if perhaps it was inappropriate to converse in graphic detail about app-enabled threesomes in the open-plan office. I stopped wearing dresses, to stanch a recruiter’s stream of strange and unsettling compliments about my legs, which he spoke about as if I were a piece of furniture. A chair without a brain. A table with shapely legs. Sexism, misogyny, and objectification did not define the workplace—but they were everywhere. Like wallpaper, like air.

“I love dating Jewish women,” he said. “You’re so sensual.” How did he know I was Jewish, I wondered, but of course he knew I was Jewish: large aquiline nose, gigantic cartoon eyeballs, eyelashes long enough to smash against the lenses of my glasses. I had the zaftig figure and ample rack characteristic of my sensual Ashkenazi kin. What did he want me to say, I wondered—thanks? Jewish people really value education, I mumbled.

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.

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.”

Those with the ear of the CEO could influence hiring decisions, internal policies, and the reputational standing of their colleagues. “Flat structure, except for pay and responsibilities,” said an internal tools developer, rolling her eyes. “It’s probably easier to be a furry at this company than a woman.” “It’s like no one even read ‘The Tyranny of Structurelessness,’” said an engineer who had recently read “The Tyranny of Structurelessness.”

The parent corporation, which employed some seventy thousand people, was a world-historical summit of engineering talent—a limitless resource to explore, an organizational marvel—but it looked, from the outside, like it was suffering from a certain degree of sclerosis. It was the best big company to work for, Ian sometimes said, but the core business was still digital advertising, not hardware.

Cities were important, he began, as if warming up for a pitch; as if we did not tacitly agree on this, standing in a living room in a famous urban center. “But cities could be smarter,” he said. “They should be smarter. What if we were given a blank slate? What problems could we fix?” Men were always talking about our problems. Who was the we? “We have all these new technologies at our disposal,” he said. “Self-driving cars, predictive analytics, drones. How can we put them together into the perfect combination?” I resisted making a joke about central planning.

I asked where the first blank-slate city would be, expecting him to say somewhere in California—outside of Sacramento, maybe, somewhere within commuting distance that would release some of the pressure from San Francisco. Central America, he said. Maybe El Salvador. “Somewhere with people who want to work hard, and don’t want to have to deal with crime,” he explained. I stared, with great interest, at the bottom of my beer bottle. “The idea is to follow lean-startup methodology. The city will start small, like an early startup that has to cater to the first hundred users, rather than the first million.” I asked how he planned to scale up, and regretted it as soon as he gave me the answer: shipping containers. To live in? I asked. What about community? People didn’t come from nowhere. What about the local economy? I was starting to get mad. I was starting to show my cards. “Ideally, it would be a special economic zone,” he said. “You know Shenzhen?” I knew Shenzhen: a high-gloss, highly surveilled city where rapid economic growth encouraged both luxury development and child-labor abuses; a citizenry partaking of modernity and progress, under dictatorial control. An epiphenomenon of authoritarian capitalism. Did he know Shenzhen? I wished I was drunker, so that I could get mean. I asked what the seed round was, intending it as a joke. They were just bootstrapping, he said. Paying mostly out of pocket—the team was still small. They just needed to raise fifteen million dollars.

There was a running joke that the tech industry was simply reinventing commodities and services that had long existed. This joke was disliked by many entrepreneurs and venture capitalists, though I thought they should be thankful for the diversion: it moved the conversation away from structural questions about why certain things, like mass transit, or housing, or urban development, had problems in the first place.

The venture capitalists were not above inspiration culture. They shared reading lists and product recommendations, and advised their followers to stay humble. Eat healthy, they said; drink less. Travel, meditate, find your why; work on your marriage, never give up. They preached the gospel of eighty-hour workweeks, and talked up the primacy of grit. Whenever they denigrated the idea of work-life balance as soft, or antithetical to the determination necessary for startup success, I wondered how many of them had an executive assistant. A personal assistant. Both. I couldn’t imagine making millions of dollars every year, then choosing to spend my time stirring shit on social media. There was almost a pathos to their internet addiction. Log off, I thought. Just email each other.

“As an example, think of the abolitionists,” she said. I asked what the abolitionists had to do with libertarian contrarianism. “Well,” she said, “sometimes minority opinions lead to positive and widespread adoption, and are good.” As a neutral statement, this was hard to disagree with. Some minority opinions did lead to positive change. I wanted to give her the benefit of the doubt. But we weren’t talking about a neutral statement. We were talking about history. I took a sip of red wine from a glass that I hoped was mine, and ventured that the abolition of slavery was perhaps not a minority position. Slaves themselves were surely abolitionists, I said. Just because no one was polling them didn’t mean they did not exist. I was trying to be lighthearted. I was trying to be kind. I was trying not to embarrass both of us, though that ship might have already sailed. The rationalist turned to look wistfully at the other partygoers, now gathered in the living room and happily instructing a virtual-assistant speaker to play workout music. She sighed. “Okay,” she said. “But, for the sake of argument, what if we limit our sample to white people?”

The novelty was burning off; the industry’s pervasive idealism was increasingly dubious. Tech, for the most part, wasn’t progress. It was just business.