Tech Is Boring: Uncanny Valley by Anna Wiener

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The first Silicon Valley startup I worked at was a stereotype brought to life via ambition and venture capital. Within the beige one-story office in Mountain View, a five-minute walk from the apartment where the company housed interns, there was a rock climbing wall, a foosball table, Sriracha peanuts, catered lunch, a MacBook hanging from the ceiling surveilling for the arrival of said catered lunch, a bench press, a squat rack, a prominent whiskey collection, a kegerator and—of course—a ping pong table. That summer, there were at least two engineers younger than me who worked full-time. I was nineteen; in engineering, there were more teenagers than women.

“I’ve seen this movie. I’ve read this book before,” Anna Wiener writes in her new memoir, Uncanny Valley. It’s a sentiment likely to be echoed by any readers who, like myself, are close to the tech industry, or have been keeping up with the news. Compared to the most sensational details on companies like WeWork or Theranos that have come out in recent years, there is nothing shocking or revelatory in Wiener’s account of startup life and culture. That’s also maybe the point.

Rather than shocking and lurid details, recognition and familiarity play a key role in the experience of Uncanny Valley. Wiener sketches out her path, originating in New York at a publishing firm and, after a brief trial period at a startup called Oyster, ending in San Francisco, working first at a data analytics startup, Mixpanel, and then at the open-source company GitHub. However, these names cannot be found in the text. Wiener omits nearly all proper nouns and refers to companies with accurate, if sardonic, phrases—Facebook, for instance, is “the social network that everyone hated.” Readers are left to fill in the gaps and see what they can see. References to The Gold Club (“a strip club… which my coworkers claimed had a superlative lunch buffet”) or Local Edition (“speakeasy, with heavy velvet curtains… newspaper themed”) read almost like Jeopardy! prompts. For those who know, they might feel like inside jokes, deprecating ones made by smarter friends that leave you feeling a little gross.

Deprecation, aimed at both the industry and the author herself, also plays a key role throughout the work. Certain paragraphs are so caustic they feel designed to be hastily photographed via mobile phone, dropped in group messages or social media feeds with captions about feeling “attacked”:

All these people, spending their twenties and thirties in open-plan offices on the campuses of the decade’s most valuable public companies, pouring themselves bowls of free cereal from human bird feeders, crushing empty cans of fruit-tinged water, bored out of their minds but unable to walk away from the direct deposits—it was so unimaginative. There was so much potential in Silicon Valley, and so much of it just pooled around ad tech, the spillway of the internet economy.

It’s undeniably enjoyable, but there is something indulgent about this sort of self-flagellation. Part of the book’s popularity in the Bay Area probably stems from this indulgence—for many, recognizing flaws within the system is enough to assuage the feeling of guilt without requiring action, reparation, or even a real admission of complicity

Luckily, Wiener offers us more than eloquent masochism. Uncanny Valley also provides precise depiction of cultural moments and movements in Silicon Valley: discrimination scandals, the obsession with optimization, data privacy concerns, the increased focus (if not clarity) on the question of content moderation. Wiener has a knack for perceiving abstract, structural issues and conveying them in specific and concrete language. For example, she discusses the problems of inappropriate content and content moderation through the lens of her work on the Terms of Service team at GitHub. Given little to no guidance on what was officially allowed on the site, Wiener notes how she, along with three (three!) other employees, attempted to essentially generate content policy as they moderated. Her team decides “nipples needed to be contextualized,” but they “weren’t trying to be puritanical.”

If one aspect looms larger than others, it is the rampant misogyny endemic in the industry. It is carefully observed in a variety of forms and a near-constant thread throughout the book. Coworkers comment on her legs, openly discuss “app-enabled threesomes” in their office, and offer unsolicited details on their racial dating preferences. Misogyny was “everywhere,” Wiener writes, like “wallpaper, like air.” It’s also one of the last thoughts she leaves us with. After the purchase of GitHub by Microsoft, some employees were able to exercise their stock options and obtain a windfall of cash at the exclusion of others, “largely women in nontechnical roles whose work had been foundational to the company,” whose lower salaries had left them unable to save enough to capitalize on their grants. Worse, some of these women “were promised extensions on the exercise windows, only to have the extensions vetoed by the board,” robbing them out of this once-in-a-lifetime opportunity. “Systems do work as designed,” Wiener adds.

By way of all this careful observation, analysis, and biting sarcasm, we arrive at a detailed portrait of Weiner herself as someone inquisitive, tender, funny, and contradictory. Some of the contradictions are simple: “I hated the success metrics, but I liked being the one who monitored them.” Others are larger and more complex, namely Wiener’s continued participation in these institutions she criticizes. It begs the question: if you hate it so much, why don’t you leave?

On the surface, there are rationalizations: It’s “just a day job.” At least it’s not finance. At least “it’s not ad tech.” At least it’s not Palantir. “I like the CEO.” There’s also a feeling of camaraderie through accomplishment with her coworkers, and a sense of hope for the future. But Wiener also provides a direct answer:

I was perhaps still afflicted by the shortsightedness of someone whose skill set was neither unique nor in high demand. A sense of my own disposability had been ingrained… quitting without a plan was unfathomable.

For anyone who came of age during the financial crisis, or who lacks the traditional safety net of family money, this, too, will be unsurprising. You don’t need to be a non-technical employee in Silicon Valley to feel the anxieties of precarity. What is surprising is Wiener’s ability to extend these analyses beyond herself and to empathize even with those who might not deserve it.

This includes the CEO of Mixpanel, a man who by her own account was “vindictive,” and “shut down our ideas and belittled us.” Rather than hold him personally responsible for his behavior, she notes how pressures not so different from her own weighed on him, who “at twenty-five… was responsible for other adults’ livelihood.” A great burden had been strapped to his back by the workings of venture capital, and she imagines him imagining his employees’ families, the mouths the company needed to keep feeding. Even though she eventually sees that unlike “the rest of us, he could never backslide,” she provides the reader with a structural answer for this as well, avoiding individual blame: “He was surrounded by people who were crushing it, and people who had chosen him. Kingmakers. People who did not like to admit defeat.”

It’s unclear where this leaves us, the answer to most of the questions posed being “widespread, structural issues.” It’s unclear it needs to leave us anywhere. Uncanny Valley is, ultimately, a memoir, and a well-written and engaging one at that. It feels greedy to want more than it gives, to want contradictions resolved to a clear path forward. Nevertheless, this is part of what I felt upon finishing: what now? What next?

After all, somehow, Wiener still seems to have hope that things can change. She believes it could come from workers who understand “the global system to which they were contributing” and who are “willing to put themselves on the line.” In a recent interview with The Guardian, discussing the decision to write a memoir rather than fiction, Wiener emphasizes that she wants Uncanny Valley to be more than an intricate self-portrait or a snapshot of a cultural moment. She aspires for “this book to be politically useful.”

Maybe part of this is possible through the writing and reading alone. Recognition can have a layer deeper than the initial thrill of familiarity, and the act of recognition might be one of validation, a form of solidarity. Multi-factor verification of a lived reality, the way someone felt. But as a solution, it all seems too passive, too cerebral.

I went to see Wiener in conversation with a well-known New York Times tech reporter in a beloved local bookstore. I hoped to ask her more about the politics of it all, of what could be done from here. It seemed particularly relevant given recent events: Over the past few years, Google employees had become increasingly restless, protesting on a variety of topics ranging from the search engine’s cooperation with the military to the mishandling of sexual harassment cases. The company appeared to be actively suppressing dissent, even firing four employees who were organizing labor movements. At Amazon, direct threats of termination were issued to climate change activists.

During the discussion, Wiener briefly mentioned increased government regulation and the leverage of worker power, but I missed my opportunity to ask any further questions. Instead, toward the end of Q&A, an audience member asked an unrelated question, and I missed it daydreaming about my senior year of college.

Over the course of my college career, I had enjoyed some of the work, loved the satisfaction of arriving at a good solution, but had always understood computer science as a means to an end. A stable, high-paying position with job security—financial independence, the end of precarity. An end achieved with a full-time offer I accepted in the fall of my senior year.

That spring, I finally gave myself a break. No computer science classes or job interviews, no learning programming languages on the side. It was the first “time off” from coding I’d allowed myself since I was sixteen years old.

I studied Asian American literature. I dabbled in figure drawing and sequential art, made messy comics about identity and interracial dating. I went to parks, art museums. I learned about Korea from the end of the Joseon dynasty through the modern day. I found a love that burned soft yellow, incandescent and illuminating. I spent more time with friends.

“Tech is boring,” Wiener responded. For all its rhetoric of disruption and innovation, the industry was—is—unimaginative, predictable, constrained by wealth and profit motive. The crowd, myself included, laughed at the gauntlet thrown, the interviewing reporter scanning the room wide-eyed, searching for expressions of shock and offense. Wiener stared out ahead.

“There could be so much more,” she said. I felt myself nodding. I still wasn’t certain on how to arrive at these possibilities, but for a moment I shared her vision; it felt concrete. And right here—between those bookstore walls, the pages of Wiener’s memoir, these words on my screen—seems as good a place as any to start.

Jefferson Lee grew up in Canandaigua, New York. He studied computer science and mathematics at Harvard University and now works as a software engineer in San Francisco. He has fiction in Maudlin House. This is his first nonfiction publication. More from this author →