‘Uncanny Valley’ Charts a Tech Pilgrim’s Progress

Books of The Times

Credit...Sonny Figueroa/The New York Times

Even at the end of a decade marked by surveillance capitalism and Russian trolls — a period of time when techno-utopianism curdled into disillusion — Silicon Valley has shown itself more than capable of delivering on one of its core promises: a frictionless convenience, at least for those who can afford it.

The journey from feeling to wanting to procuring used to take deliberation and time; now the experience has been squeezed into a seamless moment of scrolling and clicking, without any obligation to interact directly with another human being. Two decades ago, the novelist and former software engineer Ellen Ullman anticipated that the internet would bring about the “suburbanization of existence” — a libertarian idyll or libertarian hellscape, depending on how you might fare in an increasingly private and privatized world.

In her extraordinary new book, “Uncanny Valley,” Anna Wiener recounts what made her, a 25-year-old woman with an “affectedly analog” life in New York City, abandon her job at a literary agency in 2013 to work for tech start-ups, and what eventually — five years later — made her leave the industry. Money was certainly part of her original decision, but not all. At the literary agency, she was subject to the low pay and genteel exploitation of a shrinking industry; even more alluring than the offer of a better salary was tech’s “optimism and sense of possibility,” how it “promised what so few industries or institutions could, at the time: a future.”

It was this promise that initially sustained her. She worked for a few months at an e-reading app that seemed safely connected to her literary interests, though she noticed that the CEO misspelled Hemingway in his pitch to investors (adding a superfluous “m”) and accidentally typed a private message into a companywide chat room complaining that Wiener was “too interested in learning, not doing.” She moved to the Bay Area, joining an analytics start-up and later an open-source platform.

The language she was supposed to learn in her new milieu suggested that something was amiss. Wiener registered the unselfconscious deployment of hideous portmanteaus like “designpreneurs” and “blitzscaling.” The lexicon included an inordinate number of athletic and wartime metaphors, reflecting what Wiener calls “tech’s dark triad: capital, power and a bland, overcorrected, heterosexual masculinity.” People were expected to “co-execute,” and to do something called “upleveling.” Interviewing for her nontechnical job at the analytics start-up, she was asked the kind of inane question that’s supposed to assess cultural fit as much as puzzle-solving ability: “How would you describe the internet to a medieval farmer?”

ImageAnna Wiener, author of the memoir “Uncanny Valley.”
Anna Wiener, author of the memoir “Uncanny Valley.”Credit...Russell Perkins

Wiener was skeptical of all the chipper sloganeering she encountered, though she depicts herself as someone who didn’t relish the prickling sense of alienation and tried hard to fit in. She started taking B vitamins to boost her energy levels, and nootropics to boost her cognitive function. She listened to the unrelenting rhythms of EDM, “the music of the 24-hour hustle, the music of proudly selling out.” She grew accustomed to eating upscale fast casual, and purchased a pair of wool sneakers that she saw everyone else wearing in line at the food truck and in her social media feeds; the sneakers looked like “a child’s drawing of a shoe,” a renunciation of sensuality for comfort.

“Silicon Valley might have promoted a style of individualism,” she writes, “but scale bred homogeneity.” It’s exhausting to feel perpetually estranged, and Wiener felt herself slipping “into a smug sense of belonging.” She was entrusted by the CEO of the analytics firm to screen job applicants for her team, and the questions she asked indicated that her acculturation was complete: “How would you describe the internet to a medieval farmer?”

Wiener’s storytelling mode is keen and dry, her sentences spare — perfectly suited to let a steady thrum of dread emerge. Few people get names in “Uncanny Valley,” and none of the companies do. Early on in the book, she refers to “an online superstore” and “a social network everyone said they hated,” later swapping out the indefinite articles for definite ones, effectively showing how the internet behemoths have eliminated their competition.

As a woman, Wiener felt both conspicuous and invisible, valued for her contribution to “diversity metrics” while her “soft skills” were simultaneously exploited and derided. “I was always trying to be everyone’s girlfriend, sister, mother,” she writes. A male supervisor criticized her “for being a pleaser.” Not everyone, though, was expected to change. When Wiener later informed the same supervisor about a colleague’s sexual comments, he seemed embarrassed but ultimately dismissive. “You know him,” the supervisor said. “That’s just who he is.”

Wiener continued to cling to the belief that the casual misogyny she encountered masked “a yearning at the heart of entrepreneurial ambition, a tender dimension that no one wanted to acknowledge.” Surely the extravagant displays of arrogance were rooted in a profound sense of vulnerability — that what these young men ultimately wanted was something she could understand and relate to: “community or intimacy, to simply be loved and understood.”

Only later does she realize that her empathetic impulses may have led her astray. She was so fixated on trying to discern what motivated people that she lost sight of the vast, exceedingly powerful system she was participating in, and what the system was doing — not just to her, but to everybody. She was working at the data analytics start-up when Edward Snowden (referred to in the book only as “the whistle-blower”) released the trove of classified documents about government surveillance; she was working at the open-source platform when people started using it as a repository for bizarre conspiracy theories about a pedophilia ring run out of a Washington pizzeria. “I didn’t give the repository a second thought,” she writes, “until it was all over the news.”

Toward the end of “Uncanny Valley,” Wiener describes her belated realization that the tech entrepreneurs “were doing fine.” They “had power, wealth and control.” As for the rest of us — creating data that gets harvested and sold to companies that then use our data to sell us stuff — who knows? Maybe asking someone to describe the current online dispensation to a medieval farmer isn’t so risible after all. You might begin by making an analogy to feudal landlords and their serfs.