Uncanny Valley

by Anna Wiener

As he continued his pitch, it became clear to me that the utility of the e-reading app was not so much about reading as it was about signaling that you were the type of person who would read, and who would use an app with a cutting-edge reading experience and innovative, intuitive design.

“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.

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.

They looked tired, resigned, sheepish. Mostly, they looked at their phones.

“We’re looking to buy in Oakland,” one of the men was saying. “Too dangerous,” said another. “My wife would never go for it.” “Of course not,” replied the first, absently swirling his wine. “But you don’t buy to live there.”

I still clung, condescendingly, to the conceit that art could be an existential curative. That music or literature was all anyone was ever missing. That somehow these pursuits were more genuine, more fulfilling than software.

We dressed however we wanted. We were forgiven our quirks. As long as we were productive, we could be ourselves.

“You tell the bartender three adjectives, and he’ll customize a drink for you accordingly. I’ve been thinking about my adjectives all day.” What was it like to be fun, I wondered—what was it like to feel you’d earned this?

I hated the success metrics, but I liked being the one who monitored them.

He was interested in running complex data analysis on our team’s performance and holding the boys accountable to numbers. I talked about compassionate analytics. He talked about optimizing. I wanted a team of tender hearts. He wanted a team of machines.

Hiring the first nontechnical employee was always the end of an era. We bloated payroll; we diluted lunchtime conversation; we created process and bureaucracy; we put in requests for yoga classes and Human Resources. We tended to contribute positively, however, to diversity metrics.

I resigned myself to a future where, if I got lucky, my grandchildren’s college tuition would be thanks to some company that sounded like accidental metathesis, or a Freudian slip.

Being the only woman on a nontechnical team, providing customer support to software developers, was like immersion therapy for internalized misogyny.

I wanted the men on my team to think I was smart and in control, and to never imagine me naked. I wanted them to see me as an equal—I cared less about being accepted by men sexually than I did about being accepted, full stop. I wanted to avoid, at all costs, being the feminist killjoy.

The book was good, the CEO told me. If you like this, you’ll love therapy, I did not say.

We didn’t want to outgrow the company, but the company was outgrowing us. None of us had anticipated that success would be to the detriment of what made the place feel special—what made it feel like ours. The new employees treated it like any other job. The new employees had no idea.

“You’ve been with us for a year,” he said. “I ask everyone the same thing. Has this been the longest or the shortest year of your life?” Longest, I said. It was knee-jerk, sincere. His eyes narrowed, and he half laughed. At the end of the table, the solutions manager visibly eavesdropped. “It’s a trick question,” the CEO said. “The right answer is both.”

I sat across from engineers and product managers and CTOs, and thought: We’re all just reading from someone else’s script.

Job listings were an excellent place to get sprayed with HR’s idea of fun and a twenty-three-year-old’s idea of work-life balance.

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.

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 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.”

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’s like no one even read ‘The Tyranny of Structurelessness,’” said an engineer who had recently read “The Tyranny of Structurelessness.”

The male allies, all trim, white executives, took their seats and began offering wisdom on how to manage workplace discrimination. “The best thing you can do is excel,” said a VP at the search-engine giant whose well-publicized hobby was stratosphere jumping. “Just push through whatever boundaries you see in front of you, and be great.”

The consultant’s firsthand familiarity with this milieu—and her knowledge of who, from their cohort, had not accessed such fortune—suggested to me that it was not a coincidence she had dedicated her career to the Sisyphean task of proving to people in positions of power that discrimination in tech not only existed, but should, and could, be addressed.

A woman who built internal tools recommended that the men read Feminism Is for Everybody, and they solemnly nodded. It all felt like intellectually engaged, important work. I couldn’t believe I was getting paid to do it.

I knew, even as I was moving through them, that I would look back on my late twenties as a period when I was lucky to live in one of the most beautiful cities in the country, unburdened by debt, untethered from a workplace, obligated to zero dependents, in love, freer and healthier and with more potential than ever before and anytime thereafter—and spent almost all my waking hours with my neck bent at an unnatural angle, staring into a computer. And I knew, even then, that I would regret it.

“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.

How should we measure the effectiveness of a city? What are a city’s KPIs? What should a city optimize for? KPIs, optimization: it reminded me of the analytics software. Who would own the data sets, I wondered; what would they do with them?

I’d believe in an AI renaissance as soon as venture capitalists started enrolling in pottery classes; as soon as they were automated out of a job.

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.

“Okay,” she said. “But, for the sake of argument, what if we limit our sample to white people?”

A spate of experienced corporate players joined the leadership team, and a spate of them left. Leadership was a revolving door. Every few months, Engineering went through a reorganization. No one knew what anyone else was working on; no one knew who was responsible. A high-level executive came on to do strategy; when I asked a coworker what he did, I was told he set strategic meetings.

What were we doing, anyway, helping people become billionaires? Billionaires were the mark of a sick society. They shouldn’t exist. There was no moral structure in which such a vast accumulation of wealth should be acceptable.

All these people, spending their twenties and thirties in open-plan offices on the campuses of the decade’s most valuable public companies, pouring themselves bowls of free cereal from human bird feeders, crushing empty cans of fruit-tinged water, bored out of their minds but unable to walk away from the direct deposits—it was so unimaginative.

Patrick leaped up in excitement. Inside the bag, he explained, were two continuous glucose monitors with digital readers. The monitors were difficult to procure in the United States, and the readers had to be imported. We all watched as he unwrapped the package and punched a sensor into his own shoulder, wincing. I tried to exchange a meaningful look with Ian. Patrick did not have diabetes. “What?” Ian said. “Seems cool. I’d try one.”

Patrick was idealistic and independent, but it seemed that the professional demands and social mores of his structural position could eventually require that he work against himself. It was strange to see him form a public identity on social media—strange that he had followers, a fan base—and from time to time, he would endorse publications or policies or positions that surprised me. I had a hard time with this. The private person was funny, thoughtful, open-minded. But the public persona, with whom I often disagreed, had growing amplification, influence, and power.

They had inexorable faith in their own ideas and their own potential. They were ecstatic about the future. They had power, wealth, and control. The person with the yearning was me.

I could have stayed in my job forever, which was how I knew it was time to go. The money and the ease of the lifestyle weren’t enough to mitigate the emotional drag of the work: the burnout, the repetition, the intermittent toxicity. The days did not feel distinct. I felt a widening emptiness, rattling around my studio every morning, rotating in my desk chair. I had the luxury, if not the courage, to do something about it.