The Loop in the Kingdom of Vectors

Anna Wiener’s Silicon Valley memoir is beautifully observed but frustratingly vague.

Anna Wiener in a white sweater.
Anna Wiener.
Russell Perkins

In the early 2010s, Anna Wiener had an assistant’s job at a literary agency in New York. She dated the kind of artisanal Brooklyn men who “made chapbooks or live-edge wood furniture,” and, she maintains, she didn’t even have apps on her phone. She was broke, working in an industry with notoriously low pay and sparse opportunities to move up. When she read about a new startup that had landed $3 million in funding to offer e-books on a subscription model, she decided she wanted in.

Uncanny Valley, Wiener’s memoir of several years working in the tech industry—at first in New York, but soon in San Francisco—is a book that shares the in-betweenish quality its title describes. (The Uncanny Valley refers to the unsettling feeling provoked by representations of human beings that come close to resembling real people while remaining discernibly artificial.) Is it the story of a young woman figuring out what to do with her life, or is it grunt’s-eye view of an industry with immense economic power and social influence? Wiener worked for three companies in customer service positions, relatively low-status in a culture that prizes technological and engineering expertise above all. She had no interest in learning to code. When she tried, she had some aptitude but found herself “thinking about all the other things I would rather be doing, like reading a novel, or writing postcards to my friends, or exploring a new neighborhood on my bike.”

Wiener was, in other words, exactly the sort of curious, creative, dreamy twentysomething whom San Francisco, with its myriad subcultures and quasi-amateur arts scene, once seemed purpose-built to nurture. She is a born noticer, with a novelist’s knack for selecting evocative detail and compacting it into neatly turned sentences. A New York neighborhood is “tourist-addled”; a takeout lunch consists of “high-saline ramen”; the San Francisco restaurants where she dines with a CEO friend are “full of natural fibers and acacia accents, unobtrusive flora and barre-body waitresses in linen shifts; couples in their thirties and forties, the women wearing sturdy ankle boots and understated engagement rings, the men dressed, typically, to traverse a glacier.” As that last quote demonstrates, Wiener lavishes her most meticulous observational powers on the many older (and sometimes younger) people she views as enviably sure of themselves and their place in the world. To her, they are adults, stable in ways that she can’t manage—financially, professionally, emotionally.

In Silicon Valley, Wiener encounters plenty of people who possess the abundant confidence she longs for. Most of them are young white middle-class men, encased in a milieu that valorizes them as visionaries, heroes, world-changers for “disrupting” supposedly nonfunctional aspects of contemporary life from taxis to grocery stores. (It’s become a bit of a truism to ding Silicon Valley’s entrepreneurial class for inventing what MIT economist Pierre Azoulay calls “the internet of stuff your mom won’t do for you anymore,” and one of the more satisfying nuggets Uncanny Valley offers is that this really, really annoys them.) Their lives are optimized for productivity, arrows pointing in one direction, toward a reductive definition of success. Wiener is a ruminating loop in this kingdom of doubt-free vectors.

Like many young women before her, Wiener finds it all too easy to get caught up in the slipstream of purposeful men. Her first San Francisco job, for a company that produced data-mining tools, was headed up by a CEO who was a spectacularly poor manager, even for a guy in his early 20s. (Running the company was his first full-time job.) When Wiener suggested that some praise from him might help motivate the team she oversaw, he frowned and asked: “Why would I thank you for doing your job well? That’s what I’m paying you for.” Nevertheless, employees were expected to be DFTC—down for the cause—devoting themselves to the company with the fervor of guerrilla revolutionaries fighting to free their people. Everyone fixated on the leader, and Wiener convinced herself that he harbored a complex inner life and feelings for the rest of them, despite all evidence to the contrary. “I was always trying to be everyone’s girlfriend, sister, mother,” she confesses.

Someone like Wiener makes for a good spy in the house of tech, although most of what she has to say isn’t particularly revelatory. The Valley’s culture has been exceedingly well-documented: the blinkered libertarianism and naïve belief in meritocracy, the amenity-upholstered workplaces, the cult of CEOs. Despite their lofty rhetoric about changing the world, most of the companies she and her friends in the industry worked for seem to be in the business of collecting data about consumers in order to better sell them stuff. (Remarkable, given the contempt most software engineers have for marketing executives, that their products often boil down to some form of marketing.) In the early days of the data-mining startup, no one could help customers use the tool without gaining full access to the customers’ databases of their customers, what Wiener and her co-workers referred to as “God mode.” Such casual disregard for users’ privacy can only be shocking to people so oblivious to the issue that they wouldn’t be reading Uncanny Valley in the first place.

What Wiener excels at is not argument or analysis—the articulation of deep patterns or historical shifts in power and attention—but the texture of life for people in a particular and pivotal time and place. She dipped into a message board maintained by a famous seed accelerator to see what the ruling class of fully immersed Valley dwellers were arguing about: “burnout’s economic rewards,” “pop science articles on the creative potential of procrastination,” how to expertly pare down the time spent with your young children so that you get the most bang from the hours subtracted from work. She describes networking events attended by earnest, focused young men in “startup twinsets, branded hoodies unzipped to reveal T-shirts with the same logo.” She recounts how every three months some engineer new to the city would post a screed about the homeless and become the villain of the hour to the handful of old-school San Franciscans who still worked as chefs or musicians or social workers. Uncanny Valley also contains bravura extended descriptions of how the internet can turn your brain into “a trash vortex, representations upon representations”:

I careened across the internet like a drunk, tabbing: small-space decoration ideas; author interviews; videos of cake frosting; Renaissance paintings with feminist captions. Cats eating lemons. Ducks eating peas. Rube Goldberg machines, Soul Train episodes, 1970s tennis matches, Borscht Belt comedy. Stadium concerts from before I was born. Marriage proposals and post-deployment reunions and gender reveals: moments of bracing intimacy between people I did not know, and never would.

The spongelike quality of the Wiener of Uncanny Valley makes her a frustrating memoir narrator, however. While the book is never dull, it often feels as if it’s idling overlong in front of an interesting view. It has a vagueness at its center that’s only exacerbated by Wiener’s hesitation to use proper names, even when the entity being referred to—Facebook, Bill Gates, Stanford, Amazon—was never in a position to demand she sign an NDA. This comes across as coy and, worse, distracting; I spent far too much time trying to coax Google into telling me who Wiener was talking about when I should have been attending to what she had to say. If Uncanny Valley is about the culture of Silicon Valley, and not just the saga of Wiener’s postgraduate professional doldrums, how can it treat the conversational currency of that culture—the specific brands, institutions, and personalities that preoccupy it—as incidental?

But the primary source of Uncanny Valley’s narrative languor is that Wiener did not know what she wanted during the period when she worked in tech, and the desire of the protagonist is the fuel a story runs on. If the tech bros Wiener encountered hold a predictable set of opinions about how the world works, so does she, the product of a liberal arts education featuring courses on the carceral state and urban studies. When she raised objections to some complacently uttered attitude—misogyny, racism, classism, privilege—her arguments had the airless quality of an academic exercise, of stances adopted from people whose active lives consist of lecturing undergraduates. The tech guys may not live in the real world, but neither did Wiener. She and her colleagues and bosses floated above the earth on a layer of stock options, free trail mix, telecommuting, and money. To her credit, Wiener knows this. “My own psychic burden,” she remarks dryly, “was that I could command a six-figure salary, yet I did not know how to do anything.”

She quit, at last, in 2018. Yet even this momentous transition—theoretically the turning point that the memoir has been building up to—feels underplayed. “I could have stayed in my job forever, which was how I knew it was time to go,” Wiener writes. She considers the 2016 election, which she’d hoped would force a moment of truth on an industry inflated with its own self-importance as it blithely facilitated the spread of disinformation. She’d canvassed for Hillary Clinton and found that the social media feminism she’d been marinating in “did not transfer to suburban Nevada. Women stood behind screen doors and looked at us, with our clipboards and patriotic stickers and aestheticized coastal corporate feminism, and simply shook their heads.” She decided she wanted to write, definitely a good call, and now works for the New Yorker. She covers Silicon Valley, so her escape seems as equivocal as Uncanny Valley itself—the tech industry is hard to quit, especially if it gets its claws into you when you’re young and formless. But at least now Wiener can call companies and people by their names.

The cover of Uncanny Valley.
Macmillan Publishers