‘Uncanny Valley’ and the Meaninglessness of Writing About Tech

Throughout her career, Rebecca Solnit has been dogged by comparisons to Joan Didion. Never mind that the writers have peanuts in common beyond a geography—California—in which Didion didn’t even remain. As a woman writing semi-journalistic sentences of quality, Solnit is doomed to her Didion descent. (They all are. Virginia Heffernan, Anna Quindlen, Meghan Daum, Katie Roiphe, Rebecca Traister, Susan Orlean, Rachel Cusk, Michelle Orange, Maureen Dowd, Roxane Gay, Leslie Jamison, Sarah Nicole Prickett, Jia Tolentino—Didion’d, every last one.) So what’s a Solnit to do when given the opportunity to sum up the virtues of a new memoir, Uncanny Valley, by a young woman writing semi-journalistic sentences of quality? Follow tradition, of course, and enforce the homology down the generations. “Like Joan Didion at a startup,” Solnit declares. It’s right there, indelible on the book jacket.

The victim of the quasi-praise is Anna Wiener, who moved to San Francisco at age 25 for a job in tech and lived to write about it. For more than four years, between 2013 and 2018, she toiled and lounged in customer support roles, first at a data analytics company and then at GitHub. Uncanny Valley is her chronicle of that period, written with the kind of piquant ambivalence that triggers a salivary response, followed by spitting cries of Didion’s umpteenth coming, in so many modern readers. Wiener is a rock-solid writer, which Solnit’s miscalibrated, publicity-oriented blurb doesn’t change. What it does do, unfortunately, is expose the book’s foundational wobble. Didion prized her vantage as a social observer, the neurotically perceptive outsider. Wiener, who lived within yet strains to see from without, is never sure where she stands—an irresolution that’s less Didion at a startup and more the ditherings of an upstart.

Wiener recognizes the problem, or fragments of it. She makes mention of identity crises; she frets about her stance and status. Early on, as she’s packing up her Brooklyn apartment, leaving behind a nascent career in publishing for something as anti-literary as mobile analytics, a close friend wonders if she’s making the right decision. Wiener takes the moment to reflect on her split consciousness:

There had always been two sides to my personality. One side was sensible and organized, good at math; appreciative of order, achievement, authority, rules. The other side did everything it could to undermine the first. I behaved as if the first side dominated, but it did not. I wished it did: practicality, I thought, was a safe hedge against failure.

Wiener is constantly at odds with herself, consumed by warring impulses that her time in tech only comes to exacerbate. She feels like a “babysitter” or “concubine” on the job; she feels “indescribably lucky” on the job. She hates EDM (“decadent and cheaply made”); she loves EDM (“like I just railed cocaine, except happy”). She takes pleasure in learning a bit of coding; she realizes “there was nothing I needed or desired from software.” She does it in the same sentence: “I hated the success metrics,” she writes, “but I liked being the one who monitored them.” Elsewhere, on biohacking: “I wanted to be above it, but I wasn’t above it.”

Like/dislike, love/hate, inside/outside: Wiener’s formulations reach for rigor, for some deep truth about knowability, but end up wimping out. She starts arguments she can’t finish, not only with herself but with her new colleagues. She’s surprised whenever one-on-one interactions admit of nuances disallowed by her standard-issue assumptions. Billionaires are bad, except the one who befriends her. Tech bros think the same way, except her roboticist boyfriend. Perhaps these conflicts are meant to echo the Bay Area itself, a land so riven by self-contradiction it’s on the verge of spiritual collapse, but the conclusion is still unenlightening. Was Didion ever so flimsy or indulgent? Her moralities were nonnegotiable. Wiener, perfecting that New York–nourished millennial mode, can’t find new meaning, only evidence, everywhere, of meaninglessness.

To stay sane as everyone around her drinks the Kool-Aid (or butter coffee), Wiener never relinquishes her outsider status. Instead, she tells herself she’s making good on her college degree and doing sociology—tech as her laboratory. Here may be the source of the struggle. Though she lives inside the glass cage, she walks around it as though from the other side, mistaking reflections for embodied reality. She’s ruled by appearances, by looking and seeing. Observing the ruggedly dressed workforce: “They looked ready to gather kindling and build a lean-to … They looked in costume to LARP their weekend selves.” Observing commuters: “They looked tired, resigned, sheepish. Mostly, they looked at their phones.” Observing businessfolk in the Financial District: “They looked so much older than we did … They looked straight out of another era, like the nineties.” No amount of looking at something, alas, makes it come alive. (Unless you’re on drugs. Which Wiener is, at one point. You’re happy for her.)

Uncanny Valley by Anna Wiener | Buy on Amazon

Courtesy of FSG

What makes this all the more frustrating is that Wiener can write an immaculate sentence. Like the very first one, an instant classic: “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.” Rhythmical, urbane, and look at that beautiful “whom”! (High on her own fumes, though, she lets the challenging pronoun define her, using it in the book at least 15 times.) In sections on the ephemerality of software, the exigencies of telecommuting, and thought-trends in tech—rationalism, city-building, UBI—Wiener’s well-honed words pierce through the conventional chatter.

She’s also a master of the descriptive arts. A hot tub at a spa-themed party becomes “a sous vide bath of genitalia.” Trendy shoes she buys but never wears are a “monument to the end of sensuousness.” Jeff Bezos is a “chelonian ex–hedge funder.” She never actually names Bezos. In fact, she uses very few proper nouns. Aside from the occasional first name of a friend, every character or company, the ones she’s worked for as well as the ones everybody knows, is glossed with a pithy phrase. The coy ploy, in subversive deference to NDA culture, ranges from effective (“the social network everybody hated”—Facebook) to distracting (“a computer-animation studio famous for its high-end children’s entertainment”—Pixar?).

Sentence-level flourishes never add up to text-level sophistication, though. Nor do they make this memoir literary, a descriptor Wiener is clearly chasing. Beyond Didion, Wiener’s other major influence seems to be Ellen Ullman. Ullman, who fell into programming in the late ’70s and stayed at it for 20 years, wrote a masterpiece of a memoir called Close to the Machine. Just because they’re both women in tech doesn’t validate the comparison, of course, but Wiener actively invites it. She profiled Ullman for The New Republic in 2016, saying that she read Close to the Machine for the first time at 25, the same year she moved to San Francisco. Here is one of Ullman’s more startling passages, talking about a guy she dated:

His lovemaking was tantric, algorithmic. I once thought that love could not be programmed, but now I wondered. This sex was formulaic, had steps and positions and durations, all tried and perfected, like a martial arts kata or a well-debugged program. My own role in it was like a user-exit subroutine, an odd branch where anything might happen but from which we must return, tracing back to the mainline procedure. I felt again as if I’d come in on a private process, something that Brian had worked out all on his own and which, in some weird expression of trust, he had decided to show me. I should have felt dissatisfied. I should have called it off. For a time, I even looked fondly at the neat monogram on my pajama pocket where it lay on the dresser top. But again I gave in to curiosity and tenderness. He has been with himself too long, I thought.

Wiener lacks this technoliterary lyricism. Perhaps because never she cracked coding, never got close to the machine, was only adjacent to it, more looker or lurker than full-bore liver, she can’t find connections, these novel ways of seeing. Instead, she produces a dishy, readable account, full of fashionable doubt and just-so anecdotes, that mostly reiterates the well-established buffooneries and blindspots of Valley culture.

Late in the book, Wiener turns to contemporary literature for some solace, to pull herself out of the internet-fueled spiralings of her filter bubble. It offers no respite, and she dismisses it all as “beautiful descriptions of little substance, arranged in elegant vignettes.” It’s such a tidy summation of her own memoir one wonders if she’s including herself in the critique. Uncanny Valley indeed began life as a series of vignettes in the pages of n+1, with the same canny title and a clearer sense of purpose. There’s a lot more to the full-length book. There’s also, true to its core ambivalence, a lot less. Read it. Don’t read it. Love it. Hate it.

Further Reading

  • Lurking by Joanne McNeil

    Though it never quite sustains the momentum of its knockout first chapter about Google, this personal history of the internet, forthcoming in February, manages a sensitive sharpness to which more tech critics should aspire.

  • How to Disappear by Akiko Busch

    If you’re tempted, as many seem to be, by Jenny Odell’s How To Do Nothing—a book-length non-argument for stopping to smell literal roses—pick this up instead. It’s stranger and more radical, a reminder that invisibility is what keeps us alive.

  • Close to the Machine by Ellen Ullman

    Has tech ever been written about so lyrically, before or since? A programmer, a memoirist, an essayist, a novelist, Ullman’s a poet at a computer, whatever the medium.

  • Magic and Loss by Virginia Heffernan

    She’s been called the Didion of tech writing, which is ridiculous. Heffernan (a WIRED contributor) is entirely her own. Loopy and hyperliterary, she can write circles around anyone and anything.

  • Political Fictions by Joan Didion

    Overshadowed by the flashy early work and her more somber late phase, this middle-period collection of essays may be Didion’s truest triumph. She never tells you what she thinks—yet by the end you believe exactly what she does.

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