Uncanny Valley: A Memoir by Anna Wiener. MCD, 288 pages.

At the end of October, I left an archetypal tech job at a secretive and controversial big data analytics start-up, with whom I signed an NDA more binding than my marriage vows. Sixteen months prior, the company had divined my profile out of the algorithmic ether of LinkedIn, during a period in my life when the sight of my student loan repayment date would send me into days-long cycles of incapacitating self-pity. This was also, incidentally, a time when I had finally begun to do the kind of writing I found meaningful and interesting. But the work, like my debt repayments, felt slow, hard, and uncertain; it required patience and faith in the long game, two qualities which I’d never needed to cultivate before. I was growing restless; I was getting bored. I felt far from the action. I wanted my life—as Anna Wiener writes in her incisive new memoir Uncanny Valley—to “pick up momentum, go faster.”

When the tech world rang the bell, my subconscious—hungry, ambitious, curious—answered. It was the equivalent of setting down a long book to pick up your phone when its screen flashes white, then forgetting about the book entirely. The salary was transformative: after five years of Sisyphean payments which had barely covered interest, my student debt vanished in nine months flat. Every aspect of my life was subsidized by unseen venture capitalists, whose faith in my employer’s eventual profitability resulted in a sugar-daddy generosity: my rent, my errands, my meals, the spin classes I needed when those meals caused me to gain fifteen pounds. On days when the work felt exhausting or demeaning, I’d slip into a meeting room, check my bank balance, and feel a sense of embarrassingly intense relief. On days when I found myself worrying over “ethical grey areas,” the kitchen staff (always women, almost always women of color, almost certainly the company’s most diverse team) would roll through each floor with a three-tier dessert cart, proffering petits fours or miniature Croques Monsieur or honey-drizzled figs: parodic emblems of the Antoinette-ish wealth the Valley’s procession of IPOs seemed to promise.

When I left, I left with conviction, a story for another time. In the weeks after, I sat waiting for my dopamine levels to rise back to normal, for my energy to stabilize, for my sense of clarity and purpose to return. Instead, I found myself lethargic and listless, reaching for something I couldn’t name. I didn’t miss the perks, and I didn’t really miss the work itself. I did miss my co-workers, but we still lived in the same city. I inevitably missed the paycheck, but I’d known what I was giving up.

What I really missed—what I felt cut off from—was what I thought I had successfully resisted. The startup, like most tech companies, like most technology itself, had done an impeccable job of transplanting its employees’ sense of purpose. Without realizing it, I had outsourced an entire part of my brain. I thought I’d been detached and observant, an anthropologist among true believers, but a small, central part of me had believed too, and that part was now wandering the desert in a torn startup T-shirt, meekly repeating phrases like “Solve the world’s hardest problems” and “Execute the mission,” thirsty for purpose.

It was in this frame of mind that I picked up Uncanny Valley. Like many millennials who’d watched tech transform from “a fun way to flirt with your crush after school” to “an unregulated behemoth undermining democracy and perpetuating global inequality,” I had devoured Anna Wiener’s short story by the same title in n+1 more than three years prior, feverishly sending the link to everyone I knew at the time. Later, I’d send it to some of my tech coworkers over the internal company chatroom, usually receiving a meek :thumbs-up: emoji in return.

What I really missed—what I felt cut off from—was what I thought I had successfully resisted.

Having lived in Silicon Valley for four years—as a student at what Wiener describes, in her arms-length, no-names style as a “private university in Palo Alto”—and having been tech-adjacent (then tech-subsumed, then tech-sponsored) ever since, I longed for writing that could effectively capture the unimaginative hedonism and fundamental sociopathy of the current tech boom: its insistence on alienating us from everything worth having, only to sell it back to us stripped down and restructured according to the values (and, worse, aesthetics) of ahistorical libertarian vampires, whose kink for giving billions of dollars to unqualified frat boys with underdog complexes had resulted in the disruption-beyond-recognition of subtlety and flirtation and dining and travel and journalism and democracy and one of America’s great counter-cultural cities, among other things I had loved absentmindedly, as though they could be taken for granted, before I realized how quickly they would be brought to their knees.

Wiener’s “lightly fictionalized” account in n+1 was what I had hungered for: it was acerbic and funny and incredibly bleak. She zeroed in on the dissociative feeling that tech elicits in its more conscientious employees and users: the self-alienating way you can recognize that a company or a product or an experience is ridiculous and even dangerous, but still be partially seduced by it, still yield. Where other writing about tech had fallen squarely on either side of the line of hyper-dystopian cheesiness (Dave Eggers’s The Circle) or fawning myopia (Alexandra Wolfe’s Valley of the Gods), Wiener’s writing cut like acid and burned like liquor. I wanted to see the Valley doused.

The long-awaited book-length adaptation of that original story—no more light fictionalization; it’s a memoir—delivers on the promise of its first incarnation in almost every way. Inherently timely, it aims for timelessness and achieves it. Its style is of a part with the dry, affectless writing of the period that Wiener seeks to capture but goes beyond the Sally Rooney-Tao Lin axis to deliver something sharper and more complete. Uncanny Valley is a quest narrative for the “privileged and downwardly mobile” millennial, a quest without a clear purpose. Wiener, as she presents herself, has no real goals and is motivated by the vague, Pavlovian cues of the upper-middle class: a desire for work that offers a sense of purpose, the gloss of prestige, and the assurance of monetary well-being, or as she puts it, work that is “intellectually engaging . . . alongside smart, curious people.” She leaves a thankless, underpaid literary job for an early stage e-book startup in New York. When she is gently let go after a trial period, her hunger for the startup world is piqued, and she finds herself blown west into the gold rush of the Valley.

That Wiener manages to make her passive observation of this easy drifting so compulsively readable is a testament to both her skill as a writer and the distinct absurdity of her subject matter. I tore through Uncanny Valley, riveted by the wit and precision of Wiener’s observations: employees “[flank] the CEO in a semicircle like children at a progressive kindergarten”; Hacker News (unnamed but easily identifiable) serves as “the raw male id of the industry, a Greek chorus of the perpetually online”; a pair of unworn Allbirds, the dorky, excessively comfortable woolen shoe beloved by Bay Area venture capitalists (the brand again unnamed by Wiener), sit in her apartment as “a monument to the end of sensuousness.” Discussing tech bros’ obsession with the concept of “achieving flow”—a trance-like state of working, usually coding—Wiener writes, “I loved that they used this terminology. It sounded so menstrual.” Later, across a few masterful pages, she nails the feeling of mindless, ephemeral internet surfing: “Just me and my id, hanging out, clicking.” Whatever unseen surveillance cameras took in my facial expressions while I was reading Uncanny Valley on public transit will have found me squinting, laughing, manically underlining whole paragraphs, and sighing loudly with equal parts weariness and recognition.

Wiener, as she presents herself, has no real goals and is motivated by the vague, Pavlovian cues of the upper-middle class.

It is clear, early on, that Uncanny Valley has no narrative arc but time; still, I wanted to see where we would arrive. Blurbs and reviews have compared Wiener’s writing to that of Joan Didion, in particular the latter’s account of California in the 1960s, Slouching Towards Bethlehem. But Didion’s depiction was one of plainly observed horror, the journalist watching at a remove, notepad in hand. Wiener, on the other hand, approaches her subject matter not as a detached journalist but as a willing participant.

Perhaps a more apt comparison would be Christopher Isherwood’s fictionalized account of Weimar Germany, Goodbye to Berlin. There is a sense, in both books, that the narrators have detached in order to process all they are seeing; a double-edged proximity which offers clarity of vision at the cost of complicity in something ominous and inevitable, arriving just beyond the book’s end. “Psychologists might refer to this as dissociation; I considered it the sociological approach,” Wiener writes toward the end of Uncanny Valley. In the memorable closing scene from her n+1 story, which makes its way into the book-length memoir, Wiener scans photographs and video from her former employer’s over-the-top holiday party, looking for her face in the crowd, even though she knows she hasn’t been part of the company for over a year. Isherwood’s book ends with his narrator watching the faces of people walking up and down the Kleiststrasse, observing that they have “an air of curious familiarity, of striking resemblance to something one remembers as normal and pleasant in the past—like a very good photograph.”

When we read Isherwood, we have the benefit of hindsight; we know how history plays out. Wiener’s task is trickier. We’re barely beyond the moment her book seeks to immortalize. Perhaps this is why moments of Uncanny Valley—whose title seems to allude to nothing within the text itself, and instead to the feeling you get while reading it—can feel irresolute, as though the author is walking a very fine line, taking care not to offend the more powerful residents of the city she still calls home. It’s clear that Wiener is canny enough to see behind the curtain, but it can seem, at times, like she still wants to believe in the Wizard.

Describing her work at a data analytics startup, Wiener writes of her colleagues’ and bosses’ reaction to Snowden’s whistleblowing that:

The sole moral quandary in our space that we acknowledged outright was the question of whether or not to sell data to advertisers. This was something we did not do, and we were righteous about it. We were just a neutral platform, a conduit.

I kept returning to that last line as I worked my way through Uncanny Valley for a first, then a second, then a third time. Each time, I felt teased by Wiener’s occasional snark, wishing it cut deeper. For anyone who misses Valleywag, there is some coy skewering of the industry throughout, though it can feel, at times, like that skewering is being done with the dull side of a sharp knife. The pared-back tone which gives Wiener’s memoir its stylistic strength betrays a forgivable weakness at the heart of her project: at times, Wiener seems too eager to stick close to the line of neutrality, to present Uncanny Valley as a conduit itself. In one memorable scene, she talks with an arrogant amateur urbanist at a party, who reveals his plan to set up an experimental, “blank-slate” city of shipping containers in developing countries. “I wished I was drunker,” Wiener writes, “so that I could get mean.” I also wished she had gotten drunker. I wished she had gotten mean. Both in the moment and in retrospect, something holds her back.

Wiener’s tongue-biting tendency is clearest in the book’s final quarter. Through a good-natured Twitter disagreement over whether or not books should, like everything else in the Valley, be optimized for efficiency, Wiener unexpectedly befriends a billionaire named Patrick—easily identifiable as Patrick Collison, wunderkind CEO of Stripe—and the duo strike up a friendship over a series of elaborate, overly sensual meals. Wiener is aware that she tolerates behavior from Patrick which she wouldn’t tolerate in other friendships, with non-billionaire, non-CEOs. “It was easy to interrogate everyone’s relationship to power but my own,” she writes, but in her dynamic with Patrick, it doesn’t seem like she’s attempting much by way of interrogation at all.

At times, Wiener seems too eager to stick close to the line of neutrality, to present Uncanny Valley as a conduit itself.

Early on, Wiener traces her “industry origin story” to her tendency to “respond well to negging,” and this quality seems true of her throughout: she writes from the vantage point of someone eager to be liked, eager to take part—with the restraint of someone who feels lucky to be there at all. Though Wiener acknowledges that the emotional labor and “soft skills” she brings to the table are as valuable as her peers’ technical abilities, she also continues to call herself “useless,” and perpetually grants engineers and barely legal CEOs undeserved authority. When her boyfriend rightly tells her, “I think you’re underestimating what you might have that they don’t,” she sweetly evades the compliment (“You?”) and lets the point drop.

At so many moments, Wiener gets within a finger’s distance of speaking truth to power and then—points us in another direction, or ends the chapter, or describes a bread basket. Of course, speaking truth to power isn’t her project; if it were, this would be a completely different book. But there is something unnerving about a memoir that so brilliantly captures the mood and neuroses of San Francisco in the 2010s yet seems somehow still respectful, occasionally reverent. Even as Wiener critiques the Valley, there is a part of her that is protective of it, a part of her still in its thrall. The strongest ethical concerns in Uncanny Valley are voiced not by Wiener but by her activist ex-hookup, who seems to delight in mansplaining the moral quandaries of Wiener’s job to her. Again, Wiener opts to be the conduit, marking down his arguments without taking them on as her own. Toward the end of the memoir, Wiener begins to contemplate the value of unionizing in tech, but abruptly ends this line of inquiry when a colleague from a disadvantaged background points out, “We are not vulnerable people.” Fair enough, but the value of unionizing in tech is hardly to bargain for more lavish snacks and fitness offerings. Again, Wiener swerves away from the overtly political; here, it feels like a missed opportunity.

Any honest memoir of the 2010s in San Francisco is, in some sense, a memoir of loss: the get-rich-quick manufacture of millionaires has come at the cost of reckless destruction, the ripple effects of which were felt nationwide during the 2016 election, where Wiener ends her tale. But Uncanny Valley isn’t particularly elegiac: we are shown so little of the world outside of tech, the one being lost. My favorite section of Uncanny Valley is Wiener’s litany of beloved inefficiencies, a moving, paragraph-long tribute to the world of touch and scent and appetite and slowness, ending with “Warm laundry, radio, waiting for the bus,” that is set in contrast to the Valley’s vision of a world where everything “could be optimized, prioritized, monetized, and controlled.” Is it greedy that I wanted more by way of a defense for the sensuous world? Outside of her relationship, we are given so few glances of Wiener’s pre- and sub-Valley life, her non-working personhood. It’s true that while working at startups, your inner self is more or less transplanted by your working self—your value add. But it can be hard, in Uncanny Valley as in our day-to-day lives, to track what is being lost, cut out, sacrificed.

I’ve come to the view this as part of the project of the book itself: to leave us unsettled by how its narrator, like all of us, remains somewhat in the Valley’s mindset, if not its pocket. This entanglement is a feature of the system that works, as she notes, precisely as designed. In the end, for all the generosity she extends to those around her, Wiener is unsparing with herself: “Certain unflattering truths: I had felt unassailable behind the walls of power. Society was shifting, and I felt safer inside the empire, inside the machine. It was preferable to be on the side that did the watching than the side being watched.” Wiener has written an indispensable chronicle of this era in tech, the consequences of which we will all reckon with as the next decade unfolds. Still, given the Valley’s unmatched ability to avoid any sense of guilt as the world around it burns, there is no doubt in my mind that while Uncanny Valley will be read widely and voraciously throughout the empire, Wiener’s readers—techno-skeptics and technologists alike—will be able to recognize themselves without feeling indicted.

But surely someone, somewhere, eventually, will need to feel indicted. At some point, we’re going to need the sharp end of the knife.