‘Uncanny Valley’: When the Confidence Boys Took Over Everything

Anna Wiener's Silicon Valley memoir, Uncanny Valley, reveals a piratical industry choking on its own hubris and blind to the cost of its destruction.

Uncanny Valley: A Memoir
Anne Wiener
MCD / Farrar, Straus and Giroux
January 2020

At a time when there is no end of (justified) diatribes about the current state of a certain slice of New York City—glass-shrouded, artisanal-choked, mushroomed with CVSs and Citibanks and pour-over coffee shops, art pushed even further to the margins away from the engines of money—it can be refreshing to remember the city as the dream it once was. Gina Bellafante nodded to this in her recent New York Times column, about how the death of Prozac Nation author, Elizabeth Wurtzel, brought to mind memories of how a striving sliver of Generation X once believed, with some good reason, “that the right combination of talent, drive and intellectual privilege would sustain a long, materially comfortable New York life in the arts, in publishing.”

And then came the Internet. Not the goofy, glitchy, GeoCities, hippie-inspired “Net” of the 1990s that chewed up seed money and spat back little but instantly obsolete CD-ROMs, over-designed interfaces, and infinite argumentation on the old message board, The WELL. Purveyors of the newer, sleeker 21st-century Internet were less interested in expanding people’s worlds than in what they euphemistically called “Disruption.” Per Bellafante:

Technology changed everything, of course. Magazines disappeared; editorial contracts shrunk; streaming meant that writing for film or television was no longer likely to make you rich. Writing books was just going to make you poor. Fashion, once the purview of art, became the property of Instagram. All of these profound reversals crashed up against the hard metrics of the city’s soaring housing market.

In her lucid, bleak, and hypnotic memoir Uncanny Valley, Anna Wiener writes about being one of those dreaming New Yorkers who had thought she could make it in publishing as a member of the $30k a-year “assistant class”. But the rising tide of capital was pricing people like her out to the margins. And people who did not have her family advantages (no college debt, health insurance) couldn’t even make it to the margins. “It was nice to get new hardcover books for free,” she writes, “but it would be nicer if we could afford to buy them.”


Water drop by qimono (Pixabay License / Pixabay

In the face of the online onslaught, Wiener describes her circle as stubbornly analog. They hung on to flip phones, using accounts on “the social network everyone hated” only to “RSVP to poetry readings and DIY shows they had no intention of attending”. They grounded themselves “firmly in the embodied, tangible world”. Despite feeling like she was betraying something but nevertheless wanting “to feel affirmed, confident, and valued”, in 2013 Wiener took a short-lived job at an e-reading app startup.

She never quite figured out the product (beyond determining that it was “not so much about reading as it was about signaling that you were the type of person who would read”). But her anthropological fascination with the breezily confident manner with which the three crisply buttoned-up male co-founders presented themselves carried over into her next position and powers the low, purring engine of this book.

Wiener moved to San Francisco to work for an “analytics startup”—her habit of not naming any of the firms that come up (terming Amazon only the “online superstore” that “seemed to be experimenting with various ways to destroy the publishing industry”) initially seems perversely stubborn but ultimately lends the narrative an effectively unrooted, foggy, and timeless atmosphere. Glad for a new start but panicking about her lack of technical knowledge, Wiener throws herself into an entry-level customer support position with an intense focus that she later leveraged to describing this weird and woozy hinge moment.

Uncanny Valley starts out as social reportage. Wiener writes with a slightly acerbic and cool detachment about all this hazy California Dreaming (“the faux speakeasy, on the edge of a neighborhood filled with paperless offices, was newspaper themed”) that calls to mind early Joan Didion. But she threads that with her generation’s habitual self-doubt and second-guessing. Arriving in San Francisco to begin at her new job, she describes her younger self as thinking of herself as “intrepid and pioneering” but in truth “by many standards, late” to the party.

That sensation of being a few steps behind dogs Wiener through her narrative. She is forever missing out on underlying motivations. She’s surprised at the right-wing internet harassment on comment boards at an “open-source startup” company. It seemed very similar to what she had seen previously in Gamergate. A coworker responds to her pityingly, “Oh my sweet summer child. They are absolutely the same people.”

Schlepping to her first tech networking event, she watches a pair of venture capitalists in conversation while surrounded by hungry strivers and compares it to “watching two ATMs in conversation”. Making a snarky comment to an engineer she worked with elicited no response. At every crucial moment she, like most people outside of Silicon Valley and its glitzier user-facing facades in the Bay Area, was behind the curve.

Nevertheless, as the world changes under the impact of big data, analytics, and surveillance, Wiener admits feeling safe in her perch: “It was preferable to be on the side that did the watch than on the side being watched.” But that safety comes at a price. “Being the only woman on a nontechnical team,” she writes as the book pivots to darker realizations, “was like immersion therapy for internalized misogyny.” As her accidental career in tech takes on its own momentum, she begins to see more and more how and who forms the power structure of this brave new world, and it looks and sounds nothing like her.

That she and the rest of the world are paying a high price for the gilded seductions of Peak Silicon Valley resonates through this book. She offers alternately baffled and fascinated descriptions of the insanely lavish perks and impossibly juvenile antics of the entitled boyish men who controlled every aspect of this industry dedicated to removing all “friction” from everyday life. In one passage that should be studied decades from now, she describes the irony of innovative tech platforms run by the same cadre of “ambitious, aggressive, arrogant young men from America’s soft suburbs” presenting old ideas as if they were new. It was “a tedious process of returning to the original format.”

An online-only retailer of eyeglasses found that shoppers appreciated getting their eyes checked; a startup selling luxury stationary bicycles found that its customers liked to cycle alongside other people. The mattress purveyors would open showrooms; a makeup startup would open testing counters. The online superstore would open bookstores, the shelves adorned with printed customer reviews and data-driven signage.

While accumulation of warning signs can feel like precursors to a killing in an over-obvious horror movie—Wiener’s honest depiction of wanting to be carried along, goggle-eyed, by the torrent of money and ambition is understandable and relatable.

After all, who doesn’t want to be the writer who scores an invite to the last blowout dinner party before the fall?

RATING 8 / 10