Review: ‘Uncanny Valley’ serves up a biting slice of start-up life

Anna Wiener wanted to make her parents proud. Not long after she gave up her go-nowhere assistant job at a New York literary agency to work for a data-analytics start-up in San Francisco, she invited her mom and dad to sit in on an instructional webinar she was hosting, “as if to prove that I had moved away from them to do something useful.” Mom’s impressed. Well, at least she emails that she is: “‘Keep that perky tone!’ she wrote, crushingly.”

“Uncanny Valley,” Wiener’s biting and funny memoir of her days in San Francisco’s start-up salt mines during the aughts, is a story about wanting to be one thing and becoming its opposite. To want to be thought a grown-up and instead told you’re perky. To want to be part of what thinks of itself as a progressive tech-driven meritocracy and instead serve as a cog in a misogynistic bro-culture machine. To want to do good but instead serve an industry rife with exploitation. To want to make a life for yourself and instead work 70-hour weeks.

But what choice did she have? Wiener keeps returning to that question, asking it on behalf of a generation of expensively educated millennials who’ve had their ambitions hobbled by debt and circumscribed by Amazon and Google.

“Those who understood our cultural moment saw that selling out — corporate positions, partnerships, sponsors — would become our generation’s premier aspiration, the only best way to get paid,” she writes. She initially tries to keep her tech career — mostly in low-level customer support roles — a secret from her artistic and literary friends, as if it were an affair or an addiction. But it also feels like a secret everyone is keeping, or would like to keep.

But though Wiener’s feelings of betrayal are strong, “Uncanny Valley” is not an embittered tell-all about San Francisco start-up culture. She doesn’t give the names of the two main companies where she worked for four years, as if she’d choke to utter them, though she reveals enough to make them identifiable. Nor does she name the other companies that rule the industry’s sensibilities, the Facebooks and Microsofts. It’s a useful tactic. Wiener understands that all those brand names bring their own emotional weather, and in this book, she’s determined to create her own turbulence.

She wants to clarify the kind of displacement a rank-and-file worker feels amid tech culture, especially if that worker is a woman. At a party, her boss tells her he wants to promote her because he wants more women in leadership. “I didn’t think to mention that if he wanted more women in leadership roles, perhaps we should start by hiring more women,” she writes. Wiener’s style — informed, Twitter-pithy, at least a little exasperated — would read as mere snark if she weren’t such a gifted and witty observer. A staged chat between two venture capitalists felt “like watching two ATMs in conversation.” At a forced-fun spa-themed party with her coworkers, she avoids the hot tub, “a sous vide bath of genitalia.” Her disposable income goes in absurd directions: “I bought a vibrator with a USB port, because it made me feel more technical.”

Wiener’s humor is to a point: If the world she inhabits feels upside-down, it’s because it has taken baseline feelings about humanity and replaced them with algorithms determined to hoover up our personal data. Edward Snowden emerged as a whistleblower during Wiener’s start-up tenure, and she gets wise to just how intrusive the technology she’s serving has become. (“Do you think I work at a surveillance company?” she asks a confidant. “I thought you’d never ask,” he replies.)

Complaints of serial sexual harassment, such as the 2014 Gamergate controversy, revealed tech culture’s misogyny at its worst. But Wiener contends that the attitude is all-pervasive: Male programmers’ code sailed through, “while women’s code was picked apart or dismissed.” Pay gaps expand, stock options for women are restricted. Bigotry flows freely in the name of free speech. Wiener takes on a man’s name when handling support requests; it’s the only way to be respected.

The funny-angry voice that Wiener brings to “Uncanny Valley” has emerged as the prevailing tone of millennial writing and commentary — the defeated yet defiant cry in the face of being sold a bill of goods. It’s palpable in the deadpan prose of Sally Rooney’s novels; in the omnivorous essays of Jia Tolentino, who observes how commercial culture suckered a generation into confusing identity with Instagrammability; in memoirs like Jessica Chiccehitto Hindman’s “Sounds Like Titanic,” about her stint as a fake violinist for a PBS-friendly composer; in Netflix shows like Hasan Minhaj’s “Patriot Act,” which finds the funny in how young Americans get manipulated during the new Gilded Age.

If you’ve sensed that anger or lived within it, “Uncanny Valley” will speak to you as well as any book about millennial culture. Its humor is a proxy for the despair Wiener feels about tech culture’s predicament and her helplessness at doing anything about it. (Except perhaps writing about it: Now 32, Wiener left her job in 2018 and is a Silicon Valley correspondent for the New Yorker.)

All she can do is sigh about the experience: “It did leave something to be desired.”

You’ll have to look elsewhere for books that wrestle deeply with big tech’s monopolists and the economic inequality they sow. But “Uncanny Valley” ought to be read by policymakers just as closely as any set of statistics. Technology is too often an attempt to attack and exploit our humane instincts; it takes a humane book like this one to drive that point home.

Uncanny Valley: A Memoir

Anna Wiener

MCD/Farrar, Straus and Giroux: 288 pages, $27

Athitakis is a writer in Phoenix and author of “The New Midwest.”