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The Uneasy Promise of Life in Silicon Valley

Anna Wiener’s memoir captures the psychic burden of the tech worker.

Photo Illustration by Ryan Olbrysh

A couple of decades ago, it was easy to recognize a “selling out” narrative: An artist or group labors in obscurity doing good work until a corporation spots them and offers money and fame in exchange for creative control. The “suits” file the edges to make the product marketable, disappointing original fans. Any social critique disappears, swapped with messaging that’s unobjectionable when placed near commodities for sale. Art becomes advertising.

UNCANNY VALLEY By Anna Weiner
MCD, 288 pp., $27.00

This play on Faust was the central dilemma for Gen X artists, caught between the inherited DIY ethics of punk and hip-hop and a ballooning culture industry hungry for talent. The 1994 movie Reality Bites—directed by Ben Stiller, who himself quit Saturday Night Live after four episodes when they told him to stop making independent short films—captured the zeitgeist. When budding documentarian Lelaina (Winona Ryder) teases slacker Troy (Ethan Hawke) about one of his many ex-employers, he makes a crack about being fired for asking, “Are employee snacks subsidized?”

It’s harder to get the joke now. Companies trying to lure young recruits have snack pantries that would make a ’90s slacker pull up their sagging pants and tighten their fully adjustable belt. Not that they’d have to: Yuppie office attire has gone from suit and tie to free T-shirt and headphones. Indie directors now volunteer to make staid franchise blockbusters. Fine artists openly cater to the rich and powerful. Imagine a novelist spurning Oprah’s Book Club the way Jonathan Franzen did in the fall of 2001. Every comedian wants a Netflix special, and normal kids want to be viral social media stars, some going so far as to pretend to be paid spokespeople.

As Anna Wiener puts it in her new book Uncanny Valley, selling out is “our generation’s premier aspiration, the best way to get paid.” It’s not selling out, it’s “cashing in,” and who can blame anyone for that?


Uncanny Valley is Wiener’s account of her short career in tech. When the book begins, she is a flunky in literary New York, one of the “expendable,” “nervous,” and “very broke” assistants, stuck competing with interns who are literally cheaper than a dime a dozen, since they are not paid at all. Looking for something more, in early 2013 she joined the small staff (one, plus three founders) of a New York–based e­books start-up for $20 an hour—bargain basement wages for tech, a raise for Wiener. As it turned out, her job was mostly to order snacks for the four men. “I meticulously noted their preferences and tried to keep things interesting,” she writes, “a box of clementines one week, bags of cheddar popcorn the next.” Later Wiener wonders if they wanted her more for her gender than for her humanist perspective.

Before long they realize Wiener isn’t doing that much, and they fire her. Not wanting to go back to publishing with her tail between her legs, she takes her bosses up on their offer to place her in another tech job. Wiener flies to San Francisco and interviews at a data analytics start-up, where they ask her to take a section of the LSAT. After acing the test, she gets her offer: a customer support job at $65,000 a year with full benefits plus a $4,000 relocation stipend. She tells her struggling literary friends that she’s moving to try something new. “It was easier, in any case, to fabricate a romantic narrative than admit that I was ambitious,” the author writes. “I wanted my life to pick up momentum, go faster.” Haven’t we all.

Somewhat to her surprise, she fits in well. Wiener doesn’t really understand the intricacies of her company’s technology, but her customer support job only requires her to help the user figure out how they’ve used the product incorrectly and then to apologize for their mistake. Not called upon to exercise much personal judgment, she finds herself turning (not unpleasantly) into a machine. “Some days, helping men solve problems they had created for themselves, I felt like a piece of software myself, a bot: instead of being an artificial intelligence, I was an intelligent artifice, an empathetic text snippet or a warm voice, giving instructions, listening comfortingly.” When a customer tells her to check out his vacuous blog, she actually does. After three months, she’s awarded a $10,000 raise. This time they want to keep her.

For a twentysomething memoir, Uncanny Valley is remarkably chaste. Although there are hints of San Francisco’s legendary perversions, our otherwise curious narrator never dabbles. Instead, a soft-spoken Google roboticist gently takes Wiener’s hand at a party, and a euphemistic paragraph break later they’re boyfriend-girlfriend, going for couples bike rides and rolling their eyes at the orgies. Of an outdoor rave, she writes: “Sometimes it felt as if everyone had watched a highlight reel of people enacting freedom in the sixties and seventies—casual nudism, gleeful promiscuity, communal living.… It struck me as a performance from an imperfect past, a reenactment.”

But not all of the calculated excesses rub her the wrong way. When her company rents out a Michelin-starred restaurant for a holiday party—complete with Wagyu beef, lobster pot pie, and cocaine—she doesn’t fall out of her “smug sense of belonging” until she stops dancing. A company ski retreat to Tahoe is less exciting but still sounds nice, never mind the promotion and additional $15,000 raise she earns at the end of her first year. As the data analytics start-up expands, with salespeople taking up increasing physical and cultural space, Wiener looks to make a move. Once you’re inside tech, finding a new job sounds easy, and she lands at her first choice.


Wiener doesn’t name her third employer, but the company is easily identifiable as GitHub, the only open-source code repository in the Valley with an octopus-cat hybrid for a mascot. Throughout the book, she declines to use the proper names of companies and brands. This works to defamiliarize tech monopolies that we take for granted (Google is “a search-engine giant down in Mountain View,” Facebook “the social network everyone hated”), but it sometimes goes too far. I tripped over “a science fiction movie about hackers who discover that society is a simulated reality.” The Matrix?

At GitHub, Wiener catches “peak venture capital.” The company had recently raised $100 million and was spending it in non-negligible part on goofy and opulent office decor. “The decadence excited me,” she writes. “What else happened here, I wondered—what else might employees get away with?” With its remote-friendly rules, the new job allows Wiener to start disconnecting from her work emotionally. She’s up to a $100,000-a-year salary, with very little required of her beyond sending some emails and staying online.

Though she doesn’t discuss it much in the book, Wiener wasn’t just consuming internet content during this period, she also contributed to publications back in New York—including this magazine, where she first wrote about her tech workplace experience in an August 2015 review of Helen Phillips’s novel The Beautiful Bureaucrat. In that year she published over a dozen reviews and articles, not enough to make an unsubsidized living but about as many as anyone with another full-time job could hope to complete. In the spring of 2016, she published an essay in the influential New York literary magazine n+1 about her time in tech. The essay “Uncanny Valley” was dismal, biting, and revelatory. It went viral, instantly making Wiener one of tech’s few highbrow critics. By 2018, when she was ready to quit tech, she sold the book and the movie in one go.

Instead of limping back to the literary world full-time after the snack thing, Wiener returned as an author and a West Coast contributing writer for The New Yorker, cartoon headshot sketch and all. She has real money in the bank, and according to the acknowledgments she still has the gentle roboticist boyfriend, too. These details belong to a story that Uncanny Valley doesn’t quite want to tell. If selling out is “our generation’s premier aspiration,” why does she play down her success?

A sellout isn’t an exploiter. They’re the drummer who gets a real job, not the boss who inherited the company. In the ’90s, there was something at stake in the struggle to slack: to show that a suddenly unopposed capitalism couldn’t necessarily get everyone to work harder. But the slackers lost, and the coordinates that oriented their fist-shaking are inside out and backward. The culture industry is now more interested in harnessing difference than sanding it down. Tech has gathered a critical mass from every subculture on its corporate platforms, molding our social interactions into profitable shape. Sleep, yoga, and even “Slack” are productivity tools. Work no longer cuts into snack time.

Who cares if Wiener is a sellout? She didn’t abandon her critical writing. It’s hard to draw a straight line between her answering GitHub customer support emails in bed and any substantial harm, at least a straight line that wouldn’t take most of us out at the knees, too. But without the frisson of shame, Uncanny Valley would be a completely different book, and not nearly as good. This story isn’t about the history of the region or labor in the tech industry; it’s a self-conscious account of how it feels to climb up near the top of the barrel, where you occasionally lose sight of what it’s like for the crabs down below.

“Do you think you hate yourself?” a therapist asks Wiener in an intake session. We don’t get the answer, and it’s unclear whether a yes or no betrays deeper self-loathing. Better to hate your “Allbirds, never worn” life than to forget why you should.