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This review appears in our Spring 2020 issue, out now! Subscribe to receive our quarterly print issues in your mailbox.

Discussed in this essay: Uncanny Valley, by Anna Wiener. MCD, 2020. 288 pages.

IN JUNE OF 2013, I flew from Philadelphia to San Francisco to intern at a small independent publishing house whose twee aesthetic had by then begun to feel anachronistic. The internship was unpaid—one of the other students I was working with confessed he’d taken out a loan for the opportunity—but I had received a grant from my college to be there, a sum that, though it looked impossibly generous on paper, was quickly eaten up by the rent for my bedroom in a dilapidated Bernal Hill bungalow where we lit the stove with pliers because the knobs had long since broken off. Once, in a fit of financial optimism, I tried shopping at the neighborhood boutique grocery store instead of a Safeway; a single bag of cherries was priced at $17. On morning walks to work in the Mission, I passed long lines of men sporting messenger backpacks, waiting at public bus stops for private double-deckers that whisked them away to Mountain View. Through a new friend, I met a group of recent Berkeley graduates who told me about their unsuccessful application for an apartment that had been “Googled”—by which they meant that a group of tech workers had agreed to pay above market rent in order to secure it, a phenomenon apparently common enough to warrant its own nickname. By the time my internship ended in late August, I was flat broke and couldn’t wait to leave.

I recognized many aspects of this brief experience—the indignities of entry-level publishing work and those of living in a city reshaped by “young and moneyed futurists”—in Uncanny Valley, Anna Wiener’s new memoir about her pivot from New York publishing to San Francisco tech. The book first finds Wiener, who is now a contributing writer at The New Yorker, pushing paper at a boutique literary agency where she has little hope of advancing beyond the assistant level. Sick of working for peanuts in an industry in love with its own marginality, where “new ideas rarely emerged and were never rewarded,” she takes a chance on a job at a local e-book startup, despite her anxiety that she’s joining up with the very forces making traditional publishing unsustainable. 

The job quickly proves to be a bust. Wiener is let go after a short trial period, during which she spends most of her time curating the office snacks and writing “long, embarrassing, and unsolicited emails to the founders, declaring [her] passion for reading.” Nonetheless, her sympathetic bosses open their Rolodexes and set her on the path to San Francisco, where she lands first at a buzzy data analytics startup, and then at the software development platform GitHub, working in the nontechnical field of customer support. The identity of GitHub, it should be said, is inferred—companies are described throughout the book with recurring tags: “the online superstore” (Amazon), “the home-sharing platform” (Airbnb), “the ride-sharing startup” (Uber), “the microblogging platform” (Twitter). These clever obfuscations highlight how immediately recognizable yet fundamentally homogeneous most of these brands are. 

Throughout the book, Wiener skewers her surroundings with the same light touch. A stranger in a strange land, she defamiliarizes the new norms of the tech industry unquestioningly swallowed by her peers, restoring friction to a milieu devoted to eliminating it. She compares a fireside chat between venture capitalists at a networking event to “watching two ATMs in conversation.” The absurdity of this image is matched by the absurdity of her surroundings. An engineer at “a large social media company” takes her to a bar where, instead of ordering a drink, patrons give the bartender three adjectives, and he mixes a corresponding cocktail. At her first job in San Francisco, the highest compliment is to be “Down for the Cause” or DFTC: an acronym that translates roughly as an employee’s willingness to work outside of their job description, uncompensated. It’s of a piece with the “nonlanguage” that permeates Silicon Valley, “a mash-up of business-speak with athletic and wartime metaphors.” As in war and athletics, women tend to be marginalized; Wiener writes that working in customer support for an overwhelmingly male clientele is like “immersion therapy for internalized misogyny.” And it isn’t only the customers. Male coworkers make her feel like “a table with shapely legs”; one uses a smartwatch app that’s “just an animated GIF of a woman’s breasts bouncing in perpetuity.” When she trades in the young, lean startup for the older, more established one, Wiener’s catalog of microaggressions is mostly supplanted by descriptions of the eccentricity on display at her new workplace: coworkers who go barefoot, or dress in fetish gear, or recharge in sensory deprivation booths. Wiener elects to work remotely.

These salient details accrue like layers of paint, and ultimately the effect is impressionistic rather than schematic. Earlier this year, Wiener told an interviewer at The Guardian that she wants Uncanny Valley “to be politically useful,” but that desire isn’t always borne out by the text. Wiener is an unsparing observer of tech-exacerbated gentrification, for example, but the unsettling images she conjures—such as “a woman screaming bloody murder, dragging one leg, wearing nothing but a torn t-shirt emblazoned with the logo for a multinational consumer-electronics company”—tend to be registered more than interrogated. The anecdotal approach can only take her so far, and occasionally it constrains the aperture of Uncanny Valley’s critique, leaving Wiener with little to say about aspects of the tech industry that have been rendered deliberately invisible, like its reliance on a permanent underclass of gig workers, or the scandalous conditions of the factories in which its thousand-dollar gadgets are made. This cloistered point of view can lead to shallow diagnoses, as when she writes: “I understood my blind faith in ambitious, aggressive, arrogant young men from America’s soft suburbs as a personal pathology, but it wasn’t personal at all. It had become a global affliction.” It’s a lovely line—but less compelling as an analysis of the way a class of young tech scions have consolidated their power and shored up their image. If only a worldwide character flaw could account for the destruction Mark Zuckerberg and his ilk have wrought.

This oversimplification isn’t so much a failing of the book as a reflection of its form—ironic, perhaps, considering that Wiener’s choice of genre was influenced by that aforementioned political ambition (she worried that a fictional rendering might be “mistaken as satire”). Though the book is nonfiction, Uncanny Valley is not a polemic; it’s a memoir with palpable literary aspirations, the strength of which rests largely on Wiener’s elegantly disaffected style. Her restraint proves incompatible with the prospect of a structural critique of the tech industry, which has done much worse than imbue our lives with the tinge of unreality. 

Wiener does seem to anticipate this criticism, and she attempts to deflect it: toward the end of the book she muses, “Later, I would wonder if . . . I was more of a product of the tech industry—with its context aversion, and emphasis on speed and scale, its overwhelming myopia—than I wanted to admit. Or maybe it was personal . . . Maybe I wasn’t a systems thinker.” If that feels like a cop-out, it’s hard to hold it against her; the quality of Wiener’s noticing yields pleasures far beyond the analytical. But there are moments that suggest she knows more than she’s letting on. Uncanny Valley is not free of straightforwardly negative judgments about the tech industry, after all; they just tend to come from the mouths of Wiener’s interlocutors. It’s a former coworker at the data analytics startup who tells her that they were really building “a surveillance company,” and a colleague at GitHub who compares the windfall they receive when the company is sold to “a conflict diamond . . . it’s valuable, but it came at an unforgivable human cost.”

Ultimately, Uncanny Valley is suspended somewhere between life writing and commentary, and Wiener’s apparent reticence cuts across both modes—most glaringly in the book’s final section, which is hamstrung by a lack of narrative momentum as it approaches the present day. This is a common weakness of memoirs by young writers, whose lives are still wide open, resistant to the kind of closure the form desires. “I could have stayed in my job forever, which was how I knew it was time to go,” Wiener writes of the slow-motion decision to leave GitHub, a statement that doubles as a description of the book’s listless epilogue. In addition to the uncertainty of this line, so at odds with the granularity of Wiener’s best sentences, the book’s denouement feels like a missed opportunity to revisit a subplot that has largely receded from view: Wiener’s burgeoning writing career.

After all, Uncanny Valley isn’t only a memoir; it’s also a Künstlerroman, if an unacknowledged one. Before leaving New York for her first permanent tech job, Wiener enumerates the “self-protection” narratives she used to explain her defection to baffled friends: “The startup gig was just a day job . . . something to support me while I was otherwise creatively productive.” That meekly offered excuse lies dormant for 150 or so pages, until the glancing mention of a “handful of reviews” she’d written for what is clearly The New Republic (as with the euphemized tech companies, the publication goes unnamed). Then, in the epilogue, Wiener writes of her decision to leave tech for good: “I wanted a change, and I wanted to write”—which suggests that a fruitful creative life was slowly developing alongside Wiener’s airless professional one. 

Conspicuously absent from the narrative is the blockbuster n+1 essay from which Uncanny Valley is adapted, though its composition and publication fall within the period covered by the book, and I imagine writing it must have involved some difficult calculations. Wiener’s Guardian profile suggests as much: early drafts were reportedly more cautious, until editor Dayna Tortorici “encouraged her to reveal more about her former bosses without worrying about reprisals.” However lightly fictionalized the final n+1 piece was (the book jettisons this formal ambiguity), an ironic dispatch from the bowels of tech published in a lefty East Coast journal is unlikely to have endeared Wiener to the Valley’s many true believers. Yet the extent to which writing played a role in her decision to strike out on her own is not something we’re invited to linger on for more than a passing line. 

That’s a shame, because Uncanny Valley is in some ways a record of complicity—hers and our own. When Wiener writes, in the book’s penultimate section, “My obsession with the spiritual, sentimental, and political possibilities of the entrepreneurial class was an ineffectual attempt to alleviate my own guilt about participating in a globally extractive project,” it has the ring of a thesis statement. Admirably, she is forthright about the payout this participation netted her: a cool $200,000, thanks to the GitHub shares she cleared out her savings to purchase when she quit. But the experience clearly paid more than material dividends. Through “four years in startups” (the title of a 2019 piece for The New Yorker), Wiener found both artistic success and a subject matter equal to her talents. It would have been interesting to see her wrestle with everything the Valley gave her.


Jess Bergman is an editor at The Baffler.