A Tech Insider Stylishly Chronicles Her Industry’s ‘Uncanny Valley’


Credit...Jisu Choi

A Memoir
By Anna Wiener

At first, I didn’t understand why I was asked to review “Uncanny Valley,” Anna Wiener’s memoir about working for Bay Area start-ups in the 2010s. Wiener reports on technology for The New Yorker; I’ve only written about technology to say that I think social media is very bad. I’m much more interested in metafiction than metadata, not least because I’m confident I can explain what metafiction is.

But when I started reading, I realized that former liberal arts majors who halfheartedly resist the app-enabled future — mainly through willful ignorance and sweeping complaints — are the intended audience for this book. Wiener was, and maybe still is, one of us; far from seeking to disabuse civic-minded techno-skeptics of our views, she is here to fill out our worst-case scenarios with shrewd insight and literary detail. It isn’t that those of us with skill sets as soft as our hearts don’t need to know what’s going on in “the ecosystem,” as those “high on the fumes of world-historical potential” call Silicon Valley. It’s more that everything over there is as absurdly wrong as we imagine. “Tone = DOOM,” I wrote in the margins, and that was before an up-and-coming C.E.O. introduces Wiener, a new hire, to his favorite dictatorially motivational phrase: “Down for the Cause” (DFTC).

Is it weird that a C.E.O. can be considered up-and-coming? Yes, but of course everything about the new nearly normal is weird, and Wiener is a droll yet gentle guide. (Metadata is defined, comprehensibly and elegantly, on Page 43.) Divided into two parts — “Incentives” and “Scale” — “Uncanny Valley” begins across the country, where 25-year-old Wiener is a low-paid assistant at a small New York literary agency, “oblivious to Silicon Valley, and contentedly so.” “I did not know that it was nearly impossible to use the internet at all without enriching the online superstore or its founder,” she writes, substituting foreboding generalized descriptions for proper nouns, a choice she maintains throughout the book. (References to “RipStiks” — the obnoxious little electric skateboards that are a seemingly ubiquitous accessory of tech company staffers, especially indoors — remain, for some reason that I couldn’t figure out.) “I only knew that I was expected to loathe both, and I did — loudly, at any opportunity, and with righteous indignation.”

Unfortunately, she is also susceptible to tech bros’ clear-skinned optimism and willing to hypothesize the presence of humanity in places where it has gone the way of The Dodo (by which I mean the viral-animal-video website that claims to advocate for animals through the promotion of “visually compelling, highly shareable” content). She comes across an article about an e-reading start-up promising “to bring a revolution to book publishing” — one of several proposed “Netflix for books” projects that have thankfully failed to achieve Netflix-level success. Despite suspecting “a lot of fine print,” she finds herself intrigued as much by the possibility of a not-so-bleak future for the publishing industry as by the prospect of making more than $30,000 a year (no benefits). After a “series of ambiguous and casual interviews,” she accepts a three-month trial position, to the consternation of her publishing friends, who see the e-book start-up as the enemy.

[ Read an excerpt from “Uncanny Valley.” ]

Wiener frequently emphasizes that, at the time, she didn’t realize all these buoyant 25-year-olds in performance outerwear were leading mankind down a treacherous path. She also sort of does know all along. Luckily, the tech industry controls the means of production for excuses to justify a fascination with its shiny surfaces and twisted logic. She reads the blogs. “It was easier,” she writes, “to fabricate a romantic narrative than admit I was ambitious — that I wanted my life to pick up momentum, go faster.” Even two-thirds of the way through the book, when Wiener, by now established in San Francisco, is poised to “scale” by taking a customer-support job at a cutesily branded “open source start-up” with possibly “redemptive” techno-utopian roots (GitHub), she has not yet realized her “personal pathology” is a widespread affliction. An “entire culture had been seduced” by “ambitious, aggressive, arrogant young men from America’s soft suburbs.” (Wiener is from Brooklyn, a perspective that occasionally shades her narrative.)

Back in New York, when her trial period at the e-book start-up ends, she’s not asked to continue — she is, in the words of the C.E.O., who accidentally posts this comment about her in the company chat room, “too interested in learning, not doing.” Nevertheless, she’s able to assimilate to start-up culture in at least one critical way: She fails up. Her bosses help her find a new job out West, on the customer-support team of a data-analytics start-up founded by college dropouts that is hyped in tech-world parlance as “a rocket ship” and “the next unicorn.” She finds the analytics start-up’s bizarre interview questions infuriating (“‘How would you describe the internet to a medieval farmer?’ asked the sales engineer, opening and closing the pearl snaps on his shirt, sticking his hand thoughtfully down the back of his own waistband”). For years, she says, she’d wonder if she got the job because the process “had revealed a degree of obedience desirable in a customer-support representative.” In fact, she got it because one of the company’s founders gave her a section of the LSAT as the final portion of the interview, and she managed a perfect score. “I was always overthinking things.”

Anna Wiener fills out our worst-case scenarios about Silicon Valley with shrewd insight and literary detail.Credit...Russell Perkins

Wiener becomes part of the ecosystem; as a non-engineer seen as expendable, she’s eager to please and grateful for the opportunity to contribute to something bigger than herself. She tries to learn JavaScript in a weekend, an impossible project cruelly encouraged by her DFTC boss (who will, by the end of the book, burn out). She gets promotions and a small amount of equity — always disclosing the numbers, a small political statement consistent with her light blurring of company and brand identities. She wears her company T-shirts. She is subject to blithe sexism and assured, “That’s just who he is.” She goes on nature retreats and listens to electronic dance music. She buys the same glasses, Australian work boots and cashmere sweaters as everyone else, compelled to “optimize” though she’d always liked her “inefficient life.”

Yet for every “rationalist” who says things like “But, for the sake of argument, what if we limit our sample to white people?” she also meets an earnest, talented person who is almost certainly not evil, maybe. On “a microblogging platform,” she picks a fight with a start-up founder whom she sees arguing that books should be shorter so people can learn faster; in response, he invites her to lunch. They become unlikely friends, and he becomes “one of the youngest self-made billionaires.” Another friend, a software developer, claims to have leaked a set of documents that served as “an indictment of undemocratic activity perpetrated by the very rich.” So much around her is heady and amazing, and not only because she takes MDMA sometimes. Meanwhile, tragic ironies — “a search-engine giant down in Mountain View,” “the social network everyone hated,” a C.E.O.’s assertion that “big data was a hot space” — continue to accumulate in the background. Talking to a “digital-rights activist” while working for the data analytics start-up, Wiener asks him, tentatively, “Do you think I work at a surveillance company?” By this point, a “National Security Administration contractor” had long been in the news for leaking classified information. The activist replies that he thought she’d never ask.

Just as Wiener wants to believe that tech can solve the world’s problems, she is sympathetic to the Bay Area’s “new-school old-schoolers” who are “sorting out a way to live,” obsessed with “radical honesty,” “processing” and “checking in.” Yet their shared vocabulary with the corporate world’s new-school new-schoolers is telling: Both sides suffer from “a collapse of the barrier between subjectivity and objectivity.”

It’s possible to create a realistic portrait of contemporary San Francisco by simply listing all the harebrained new-money antics and “mindful” hippie-redux principles that flourish there. All you have to do after that is juxtapose them with the effects of the city’s rocket-ship rents: a once-lively counterculture gasping for air and a “concentration of public pain” shameful and shocking even to a native New Yorker. Wiener deploys this strategy liberally, with adroit specificity and arch timing. But the real strength of “Uncanny Valley” comes from her careful parsing of the complex motivations and implications that fortify this new surreality at every level, from the individual body to the body politic. By the end of the book, she shows that technologists are not interested in “systems” thinking only because it can fix what’s broken; they are “settling into newfound political power,” with armies of trolls now serving as foot soldiers in what founders call a “war” for market share.

Being skilled at deconstruction is a disadvantage for a customer-support specialist hoping to find “meaning” in her work, and for a millennial who values moving through the world with a clear sense of right and wrong. For a writer, though, it’s a pickax, and we’re living through a gold rush, as they might say in San Francisco.