In the Sunday Styles section of the New York Times on January 12, 2020, an article headlined “The Campus Techlash” reported that “college seniors and recent graduates looking for jobs that are both principled and high-paying are doing so in a world that has soured on Big Tech.” Readers of Anna Wiener’s wise, witty and ultimately rueful memoir, UNCANNY VALLEY --- distracted by the glittering surface of the world that the denizens of Silicon Valley have delivered to us --- may walk away from it as converts to that point of view.

Wiener’s fast-paced book chronicles her five-year journey in the tech world, one she entered at age 25 after leaving a low-paying job in a small New York literary agency. By the time she departed the open source startup where she worked for three-and-a-half years, she was pulling down a six-figure salary and, after her departure, was able to cash in some $200,000 in stock options when the company was acquired by Microsoft, identified only as a “highly litigious Seattle-based software conglomerate,” a locution Wiener resorts to in a wry if halfhearted attempt to disguise it and companies like the “social network everyone said they hated but no one could stop logging in to.”

Wiener, a self-described “sociology major with a background in literary fiction and three months of experience in snack procurement” after an abortive three-month trial employment with a Manhattan startup developing an e-reading app, finds her way to San Francisco, a “late capitalist hellscape,” marked by “a shameful juxtaposition of blatant suffering and affluent idealism,” as she describes it. There, aided by a recommendation from one of the app’s founders, she lands a customer support job with a data analytics company, where she becomes the 20th employee (and only the fourth woman, a subject that’s central to her memoir).

"...[a] wise, witty and ultimately rueful memoir... [N]ow that [Wiener is] outside, writing about Silicon Valley, startup culture and technology for The New Yorker, the rest of us will be the beneficiaries of her keen intelligence."

Displaying the bracing self-awareness and candor that makes UNCANNY VALLEY so refreshing, Wiener describes her gradual disillusionment with the culture of a company that relentlessly demanded its employees be “Down for the Cause,” and where she realized, when her salary increased from $65,000 to $90,000 after only one year, that “money was a salve, not a solution.”

After Edward Snowden’s leak of classified information about U.S. government surveillance, she began to understand that the work she was doing --- especially when she shifted into what her company called “God Mode,” which enabled her to see actual data sets that clients collected on their own users --- made her complicit in that same surveillance world. She muses uneasily at one point whether “the NSA whistleblower had been the first moral test for my generation of entrepreneurs and tech workers, and we had blown it.”

Wiener eventually departs for the open-source startup GitHub, which grows from 200 to 500 employees (only two of them black, she notes offhandedly) during her tenure, despite being implicated in a highly publicized gender discrimination scandal. She serves as what the company nicknames a “Supportocat,” where her job seems to involve little more than endless hours of surfing the “collective howl” of the internet. In contrast to her boyfriend, Ian, a software engineer who works in robotics, she admits she suffered under the “psychic burden” that “I could command a six-figure salary, yet I did not know how to do anything.”

Describing herself at one point as the “feminist killjoy,” Wiener paints an unsparing portrait of Silicon Valley’s male-dominated tech culture. “Sexism, misogyny, and objectification did not define the workplace --- but they were everywhere,” she writes. In a final reluctant gesture of surrender, she even resorts to using male pseudonyms in her work. “Men, I saw, simply responded differently to me. My male pseudonyms had more authority than I did.”

Toward the end of UNCANNY VALLEY, Wiener strikes up a friendship with “Patrick,” a tech company CEO. A little detective work (including a glance at Wiener’s acknowledgements) reveals him to be Patrick Collison, the polymath founder of Stripe, an online payment processing platform, and a billionaire by age 30. Over a series of friendly encounters, the two young people smartly debate the good and evil of the tech world. Recognizing she’s been in that world though never of it, Wiener acknowledges that when it came to Patrick and his friends, “I envied their focus, their commitment, their ability to know what they wanted, and to say it out loud --- the same things I always envied. They were all so accomplished, and athletic. It didn’t help that I hardly understood what most of them did, I just knew they were good at it.” And while these “young men of Silicon Valley were doing fine,” Wiener concedes, “the person with the yearning was me.”

By early 2018, Wiener decided she’d had her fill of what she calls “tech’s dark triad: capital, power, and a bland, overcorrected, heterosexual masculinity.” And though she admits she’d “felt safer inside the empire, inside the machine,” believing it was “preferable to be on the side that did the watching than on the side being watched,” now that she’s outside, writing about Silicon Valley, startup culture and technology for The New Yorker, the rest of us will be the beneficiaries of her keen intelligence.

She’ll have much to write about. Whether it’s concerns about privacy, the baneful effects of social media or simple smartphone addiction, for many the bloom of the technological rose has long since wilted. For all the self-assurance of the technocracy’s acolytes, it will take more than an app to cure those ills.