Tech, Please!

Uncanny Valley BY Anna Wiener. New York: MCD/Farrar, Straus and Giroux. 288 pages. $27.

The cover of Uncanny Valley

The best pieces of long-form journalism are those where you get the sinking feeling the subject has no idea what the point of journalism is. No inkling that a salacious story is better than a puff piece. No fundamental understanding that a writer, at the end of the day, is only going to make her career if she exploits her subjects, even if it’s just to expose their bad personalities or unkempt apartments. It thrills to read a story that no one wants written about themselves. Whether you are party reporting or writing profiles, you can always find something unethical to unearth, if you care to dig. And yet the majority of writers are incapable of figuring out what it is they are looking at, too lazy to suss out the implication or injustice lurking beneath the surface.

It is occasionally the case that subjects find themselves in the unique position of being written about without knowing they are in the presence of a writer. Thus, the workplace memoir. Jobs that birth writers tend to be inspiringly exploitative. Alluring for access and proximity to power, debilitating for reasons of incompetence or abuse. The underlings feel that they alone are witnessing the hypocrisy, outlandish expenditures, and dirty secrets of powerful people. There are tell-all books by nannies (Mary-Kay Wilmers’s), assistants (Anna Wintour’s), gallery girls (Gagosian’s), more juicy than substantive. They feel that their story has not been told, even if it is a story as old as time.

An anomaly is Uncanny Valley, a breakout first book by Anna Wiener about her four years working expendable non-coding positions in Silicon Valley start-ups. She was seen as dispensable; her memoir is anything but. If Silicon Valley had seen her potential, she would not have become one of the finest, most assured writers about the internet today. I read it in one sitting, overcome with the eerie sensation that my own life was being explained to me. This is a book about how in the past ten years Silicon Valley has built the very “scaffolding of everyday life.” Packed neatly in its pages is a primer on start-ups and the unicorn boom that birthed everything from Uber to Venmo, an investigation of incompetence, ambition, patriarchal impulse, and entitlement run amok, and a rumination on San Francisco and the culture created by its “nascent neomillionaire class.”

The experience of onboarding is smoother in this memoir than most. Wiener does not dwell on her childhood, except to establish her class background (upper middle). I had the distinct feeling that everything she said applied to me, despite the fact that I did not attend a math-and-science magnet in Manhattan, I don’t have a safety net from my parents, and I couldn’t get a perfect score on the LSAT without prep (at one start-up, she arrives for an interview and is handed the test instead). The seductiveness of Wiener’s writing is the feeling that we’re as smart as she is. This book is proof enough that we are not. But it taps into our lived experience: We all use the internet for the majority of our waking hours, and have no idea how it really works. “Mostly, I wrote emails for a living. Mostly, I worked from home. The job asked so little of me, I might have forgotten I had it—except for the fact that it required me to be online.” Sound familiar? “Every company wanted to build an app that users were looking at multiple times a day. They wanted to be sticky stickiest. . . . Most of the company was under the age of thirty, and we had been raised on the internet. We all treated technology like it was inevitable.” (When she mentions this phenomenon to a colleague, he shrugs it off, noting, “We already call our customers ‘users.’”)

Our desire to have the internet—and thus our lives—explained back to us by millennial women is a thrilling trend. Where Jia Tolentino has cornered the user experience (what it feels like to scroll through Instagram), Wiener ventures into new territory, breaking down the day-to-day of a tech worker (what it feels like to work in a male-dominated industry in “a late-capitalist hellscape”). Sick of the traditional publishing industry—where Wiener’s work is frustrated by the reality that she won’t get a raise or promotion—she jumps ship to a tiny start-up in New York, where she suddenly finds herself a nurse toiling in an industry rife with surgeon egos: “It was a moment of corporate obsequiousness to young men.” Against instinct (or perhaps yielding too much to instinct), she worries about the boy bosses at this publishing start-up. “Like the patron saint of mislaid sympathies, I speculated that perhaps they were just lonely. They were, of course, not lonely. They were focused and content. All three were cleanshaven and had good skin.” They saw no disjunction in trying to make an e-reading app when they didn’t like books or know about publishing. (“‘Hemingway’ had been misspelled in the CEO’s pitch deck: two m’s.”) They fire her for not making herself irreplaceable. Too proud to slink back to publishing, she heads to Silicon Valley.

She’s embarrassed by her desire to work there, aware that she is driven on some level by greed and pride, this desire to have a job that no one else understands. How else to explain moving across the country to work in a dystopian and toxic place? She later realizes this embarrassment was misplaced. “In reality, I was not paying attention: those who understood our cultural moment saw that selling out—corporate positions, partnerships, sponsors—would become our generation’s premier aspiration, the best way to get paid.” She gets a job in customer support at an analytics start-up that tracks consumer behavior, a non-coding position that was impressive only to her non-tech friends back home. At one start-up’s monthly networking “salon,” she comes to terms with her new surroundings: “I’d never been in a room with so few women, so much money, and so many people champing at the bit to get a taste. It was like watching two ATMs in conversation.”

The crux of Wiener’s book is her accidental proximity to the defining issue on the internet today: privacy. Looking back, she never pretends to have understood something she did not understand. Working at an analytics start-up, she could log in to “god mode” and look at what consumers had purchased, and yet “we didn’t think of ourselves as participating in the surveillance economy.” When she recalls working at one tech company—never named, but clearly GitHub, the open-source database and accidental internet community—she wonders how she and her colleagues missed the rise of Gamergate, for which the platform served as a breeding ground. Reading the book is like having this awakening in real time. We realize her complicity slowly, and in spurts. Like all people who have worked behind the internet, she starts to feel a little paranoid about the internet. (The internet is a little bit like sex in that the safest option is to avoid it entirely. The threat of malware—and other digital STDs—is mitigated, of course, by the knowledge that most can be cured. Usually. Unless you get doxed.)

The most affecting scene of Reality Bites is when unemployed and aimless Winona Ryder—ostensibly the valedictorian of Columbia University—cannot define “irony” in a job interview. The ability to explain something that everyone already knows is a journalistic skill valued only by other journalists, who are acutely aware of how hard it is to make sense. (Successful labor is so often invisible labor.) Wiener is not drawn in by hyperbole or flashiness. She is not preoccupied with making herself look good or clairvoyant, refusing the temptation to rise to the tenor of jeremiad. It’s clear how easily this book could slip into parody, and she does document the idiosyncrasies of her colleagues, and the California-centric rituals of technocrats (from LSD to biohacking), but never without centering herself in the narrative as complicit or jealous.

She excels at occupying several points of view all at once, a skill that results in a very charming and effective stylistic move where she positions ideas from a 3-D standpoint. Her first tech job, for example, was located “in a neighborhood the CEO called Nolita, the CTO called Little Italy, and the CPO called Chinatown.” Reading the biography of a start-up CEO, who describes himself as an optimist, she wonders: “In the Candide way, the Jeffersonian way, or the Oscar Wilde way?” Of the tech industry, when she joined it: “Depending on whom you ask, it was either the apex, the inflection point, or the beginning of the end for Silicon Valley’s startup scene—what cynics called a bubble, optimists called the future, and my future coworkers, high on the fumes of world-historical potential, breathlessly called the ecosystem.” It’s like watching an idea come alive in the round.

The experience of having a corporate job is uncanny. It makes one starved for irony. Wiener listens to bosses give “inspirational talks about the toxicity of meetings and wax poetic about the transcendence of collaboration.” She monitors self-serious discussions by men on “how to preserve mental cycles, how to achieve a state of Deep Work. . . . They talked about Stoicism as a life hack. They teetered on the brink of self-actualization.” After a few years in San Francisco, she goes to a women-in-computing conference (“I was not really a woman in computing—more a woman around computing; a woman, with a computer”) to complain in peace. Why were men like this? Why did it feel like we are dating our workplaces? I would guess that both parties in such a relationship act like their partners are valued and important while exploiting them, but Wiener doesn’t present information so didactically. “It’s probably easier to be a furry at this company than a woman,” one participant notes, rolling her eyes.

Every workplace book is ultimately about the limits of camaraderie and the limitless human capacity for tedium and abuse. What is exciting about a tech job at first—we’re changing the world! we’re the best in the world!—soon reveals its implications: At what cost to the consumer? At what cost to the employee? At what cost to the world? (“Several of my teammates’ partners had issued moratoriums on CEO-centric conversations. He was expensive to work for: at least three of my coworkers met with therapists on a weekly basis to talk through their relationships with him.”) When Wiener and her colleagues complain about the toxic work culture over drinks, one coworker just shrugs, “Look up sick systems. . . . Look up trauma bonding.” This is life with a full-time job. This book is clear: Workplace culture might be the defining oxymoron of our time.

Kaitlin Phillips is a writer from Montana living in Manhattan. You can read her Bookforum syllabus on workplace novels here.