Uncanny Valley: A Memoir

“What was my value? Five times as much as our new office sofa; twenty orders of customized stationery. While my future peers were hiring wealth advisers and going on meditation retreats in Bali to pursue self-actualization, I was vacuuming roaches off the walls of my rental apartment, smoking weed, and bicycling to warehouse concerts along the East River, staving off a thrumming sense of dread.”

Questions of value—both in terms of self-worth and aesthetic, cultural, and social value—drive Wiener toward the tech industry, out of a stagnant position in the shrinking publishing industry. This passage crystallizes her core anxiety: Unable to define her own worth, she begins to seek validation via salary, social status, and a sense of social relevance or higher purpose.

“I sat in [the interviewer’s] wake, wondering what I was waiting for. There was not a doubt in my mind that I would not get the job. Not only had I surely demonstrated that I was unemployable, but I felt certain I’d been a vivid caricature of the dotty, linty liberal arts major—the antithesis of all that the tech industry stood for. Still, though the interviews had been inane, they only served to fuel me. Here was a character flaw on parade, my industry origin story: I had always responded well to negging.”

Early in the narrative Wiener demonstrates a habit of appraising herself through the eyes of others. After enduring an absurd interview that resembled hazing, Wiener reveals that the subtle disrespect of the exercise motivated her further. With humor and painful self-awareness, her narration admits that this trait—in her eyes, a flaw—is part of what drives her to stay in the industry. 

“The home-sharing platform offered an aspirational fantasy that I appreciated. Across the world, people were squeezing out the last of strangers’ toothpaste, picking up strangers’ soap in the shower, wiping their noses on strangers’ pillowcases. There I was as I had always been, only sleeping in a stranger’s bed, fumbling to replace a stranger’s spring-loaded toilet-paper holder, ordering sweaters off a stranger’s Wi-Fi network. I liked examining someone else’s product selections, judging their clutter. I wasn’t thinking about how the home-sharing platform might also be driving up rents, displacing residents, or undermining the very authenticity that it purported to sell.”

This passage illustrates the first of many uncanny experiences Wiener has as she settles into life in Silicon Valley, stirring up simultaneous feelings of intimacy and alienation. She uses repetition to emphasize the way these odd, surreal actions—living, as if at home, in stranger’s houses—are happening not only to her but globally. She admits ignorance as to the way the home-sharing platform adversely affects local economies and communities; similar admissions of naïve ignorance become a refrain throughout the first half of the book.

“Every three months a different engineer or aspiring entrepreneur, new to the city, would post a screed on a blogging platform with no revenue model. He would excoriate the poor for clinging to rent control and driving up condo prices, or excoriate the tent cities by the freeway for being an eyesore. He would suggest monetizing homeless people by turning them into Wi-Fi hotspots. He would lambaste the weak local sports teams, the abundance of bicyclists, the fog. Like a woman who is constantly PMSing, a twenty-three-year-old founder of a crowdfunding platform wrote about the climate.”

Here, Wiener captures a tenor of entitlement, disdain, and sexism common to young men arriving in Silicon Valley for the first time. Such newcomers both drive gentrification in the city and betray a total insensitivity to its human consequences. This passage contains one of the first of many examples of the industry’s vocal but oblivious misogyny, unique in its pretense of high-minded analytical thinking while casting itself into the public forum with an exceptional lack of tact or self-awareness.

“Work had wedged its way into our identities. We were the company; the company was us. Small failures and major successes were equally reflective of our personal inadequacies or individual brilliance. Momentum was intoxicating, as was the feeling that we were all indispensable. Whenever we saw a stranger at the gym wearing a t-shirt with our logo on it, whenever we were mentioned on social media or on a client’s blog, whenever we received a positive support ticket, we shared it in the company chat room and we felt proud, genuinely proud.”

“The CEO was with us without being with us […] We drank a glass of wine each, taking small, slow sips. We discussed books we were reading or had purchased with the intent to open, as soon as we had the time. We agreed, liars both, that we would attend a second-run theater production together. We smiled half-apologetically into the conversational silence as we rolled the wine around in our mouths, as if we were drinking something more sophisticated than the house white. Eventually, we finished our drinks, and with a seamless, unspoken intimacy, both declined the waiter’s offer of a second.”

Wiener’s first months in San Francisco are solitary, and her first attempts at building a social life take on an odd air of inauthenticity. Here, on an arranged “girl date” with her boss’s girlfriend, Wiener rhythmically describes going through the motions of dinner with the woman as if it were an elegant choreographed dance piece, emphasizing its performative nature. The absent CEO looms between them as another example of how Wiener’s job intrudes on her personal life and her sense of identity.

“In Silicon Valley, non-engineers were pressed to prove their value. Hiring the first nontechnical employee was always the end of an era. We bloated payroll; we diluted lunchtime conversation; we created process and bureaucracy; we put in requests for yoga classes and Human Resources. We tended to contribute positively, however, to diversity metrics.”

Wiener raises the question of her value again as she settles into her new job—this time not in simple monetary terms, but in the context of her contributions to the company. Having taken the position to “increase” her value, she nevertheless notices the way she is viewed as inessential to the core work of the company. In this passage she betrays the fact that she has internalized the outlook of the industry and the company, denigrating her own role from the perspective of her more technically oriented, “valuable” coworkers.

“What was anyone ever talking about? People said things like ‘co-execute’ and ‘upleveling’; they used ‘ask’ and ‘attach’ and ‘fail’ as nouns. They joked about ‘adulting.’ They substituted viral memes for social currency. They deployed internet slang as if it constituted a vocabulary—as if acronyms weren’t already standing in for other words. ‘You know that animated GIF of the stick figure?’ a coworker in his early twenties asked, to describe his emotional state. I did not. ‘Lol,’ he said, not laughing. Ha, I said. Not laughing.” 

This passage marks a turning point in the narrative in which Wiener connects to her personal taste and discretion as she finds herself frustrated by the vernacular produced and proliferated by the tech industry. She points to the lack of precision in much of the language used around her every day, betraying a more unsettling vacuum of meaning and understanding. The last exchange is particularly unsettling, with the repetition of “not laughing” underscoring the lack of emotion beneath the veneer of a supposedly warm exchange. 

“I looked over at the CEO. How was this person my boss? He was just a kid. I knew he was a first-generation American, a child of Indian immigrants. He mentioned, not infrequently, his parents’ hope that he would finish his undergraduate degree. I wondered what he thought about his liberal arts employees looking for affirmation and meaning in work; if he found me spoiled and annoying. I wondered if he thought about his employees much at all. I wondered whether I’d ever understand what he had at stake, or even what he wanted.”

Wiener fantasizes about the inner lives of founders and CEOs, mystified by their status, drive, and achievements. This passage encapsulates both a moment of recognizing her boss’s emotional opacity and longing to know his deeper motivations. By contrast, Wiener’s narration sidelines her own subjectivity, opinions, and intuitions until she becomes so unhappy at the company that she is forced to confront her own desires.

“Sexism, misogyny, and objectification did not define the workplace—but they were everywhere. Like wallpaper, like air.”

Workplace sexism in Silicon Valley arises alongside its ethos of recklessness and unapologetic commitment to one’s ideas. Wiener longs to fit in at the mobile analytics company and at first ignores some of the issues she experiences as a woman at work. This brief quote captures the difficulty of naming and identifying these unequal gender dynamics in her workplace; her simile here emphasizes that the sexism exists not in isolated incidents by individual actors but something more insidious, inescapable, and structural.

“‘The worst part,’ Parker said, ‘is that the technology is getting worse every day. It’s getting less secure, less autonomous, more centralized, more surveilled. Every single tech company is pushing on one of those axes, in the wrong direction.’ My throat felt like acid. Hey, I said, and paused. Parker looked over at me. Sugar dotted his lower lip. Do you think I work at a surveillance company? I asked. ‘What a great question,’ he said. ‘I thought you’d never ask.’” 

As she tires of her work at the mobile analytics company, Wiener questions the ethics of its vast and unchecked data collection practices. Her old friend, Parker, a “digital rights activist,” names the ethical trajectory of the work being done in Silicon Valley. This passage ends the chapter, creating a suspenseful moment: Wiener breaks her passive absorption of company rhetoric to ask Parker this question. Parker seems that he’ll confirm her fear, but Wiener leaves the reader to imagine his answer.

“‘I’ve decided you aren’t analytical,’ [the CEO] said. ‘I don’t think we have the same values. I don’t even know what your values are.’ […] Despite my best efforts, I cried twice in the meeting, leaving in the middle to grab tissues from the bathroom, dodging looks of concern from the Engineering cluster. I leaned against the sink and wiped my face with a paper towel, as I had seen every other woman at the company do at one point or another. I thought about my friends back in New York. I thought about how hard I’d worked, and how demoralizing it was to be told I had failed. I thought about my values, and I cried even more.”

In a manipulative move meant to scare Wiener into contributing more at the company, the CEO questions her abilities and her value set. One of her only emotive scenes in the book, the confrontation reveals the ongoing crisis of self-worth and personal values that Wiener has yet to resolve, despite her generous salary. This pivotal interaction pushes Wiener to contemplate and then act upon an impulse to leave.

“All this time, and I could just leave. I could have left months ago. For nearly two years, I had been seduced by the confidence of young men. They made it look so simple, knowing what you wanted and getting it. I had been ready to believe in them, eager to organize my life around their principles. I had trusted them to tell me who I was, what mattered, how to live. I had trusted them to have a plan, and trusted that it was the best plan for me. I thought they know something I did not know. […] 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.”

Immediately after leaving the mobile analytics company Wiener—both as protagonist and narrator—reflect here on how and why she had become so entangled in a job that was not a fit. She sees with new clarity her previous tendency of discrediting her own point of view in favor of others’. These reflections leave Wiener-as-protagonist with more motivation to find stability, maybe even fulfillment, as well as a more cautious approach to her next job and the industry; but, in her narration, she notes that she failed to see the broader system or the global scale at which her initial mistakes were being repeated. 

“I did envy these early employees, their inside jokes and well-deserved pride. Sometimes, reading their banter or seeing photos of their children dressed as the octopus-cat for Halloween […] I would think about my foregone institutional authority, or the stack of data-driven T-shirts I kept folded beneath my towels, and feel a jolt of nostalgia. Desire. Corporate loneliness. I would yearn for the sense of ownership and belonging, the easy identity, the all-consuming feeling of affiliation. And then I would remind myself: There but for the grace of God go I.” 

Beginning work at the open-source startup, these pangs of jealousy test the progress of Wiener’s emotional journey towards greater contentment and self-knowledge. She initially feels yearning for such a relationship to the company—and, with the old T-shirts still folded in her apartment, it seems she has not entirely let go of her last job. However, she reminds herself of how trapped she felt when she allowed herself to be so immersed in a job; she alludes with dark humor to a quote by English Reformer John Bradford as he watched a group of prisoners go to their deaths. 

“I knew, even as I was moving through them, that I would look back on my late twenties as a period when I was lucky to live in one of the most beautiful cities in the country, unburdened by debt, untethered from a workplace, obligated to zero dependents, I love, freer and healthier and with more potential than ever before and anytime thereafter—and spend almost all my waking hours with my neck bent at an unnatural angle, staring into a computer. And I knew, even then, that I would regret it.”

Wiener’s creeping sense of remorse about her professional choices grows more palpable in the second half of the narrative. As her sense of self grows stronger, she struggles with work that feels physically disengaged and ethically questionable. This passage sets the reader up for a more sentimental statement, relishing the litany of privileges Wiener enjoys, before breaking the rhythm and tone of the sentence with a grotesque image and a blunt, truthful statement of regret, undermining the supposed value of her privileges and comforts.

“Everything was simultaneously happening in real time and preserved for posterity, in perpetuity.”

Wiener lyrically captures the impact of the tech industry’s products and culture on society at large: how time, conversation, and perception seem warped to Wiener and to everyone she knows. She summarizes the anxiety-producing reality of life on the internet: heightened attention of the fleeting present moment, combined with an unprecedented ability to document and archive all such moments, collapsing the barrier between an event and a record of it, between past, present, and future.

“I went to New York. On previous trips home, when I was still working at the analytics startup, the city had felt fraught with paths not taken. All these past selves, marching around like they knew something: casting aspersions on my all-encompassing tech-centric identity; trying to convince me I had made a mistake. This time, I felt lighter. […] I drank coffee with my mother until the coffee ran out or ran cold; visited my grandparents in apartments that hadn’t changed for decades. I tried to clear out the storage space in the basement, unearthing old bomber jackets with hand-sewn patches, undergraduate writing, a jar of peeled potatoes stockpiled fifteen years prior in preparation for Y2K. Banal activities, but they felt so good. I felt myself returning to myself.”

Wiener describes a more conscious and confident sense of self in her visit to New York, having matured beyond a fixation with alternate scenarios or self-critical denigrations of the path she chose. Her simple descriptions of tactile, intimate moments and objects contrasts the speed, overstimulation, and more complex language she uses describing her life in San Francisco. As the narrative pushes ahead towards a final reckoning with her work in the tech industry, this passage offers a respite and a hopeful note, implying that there is a rich world outside Silicon Valley, despite its myopic view of itself. 

“‘Progress is so unusual and so rare, and we’re all out hunting, trying to find El Dorado,’ Patrick said. ‘Almost everyone’s going to return empty-handed. Sober, responsible adults aren’t going to quit their jobs and lives to build companies that, in the end, may not even be worth it. It requires, in a visceral way, a sort of self-sacrificing.’ Only later did I consider that he might have been trying to tell me something.” 

Wiener debates Patrick at dinner as they grapple with the characteristic recklessness and self-serving nature of much of the industry’s creations. Patrick offers a concise and clear-eyed perspective on why Silicon Valley functions the way it does, while Wiener resists its nature as a matter of principle. Here, Patrick offers a subtle insight—not into the industry, but into Wiener’s personal relationship to Silicon Valley.

“When I failed to demonstrate surprise [about widespread data collection and surveillance], or tried to explain what was happening, or even admitted that some of this was actually related to the work I had done at the analytics startup, my friends’ reactions made me feel like a sociopath. These conversations didn’t make me feel superior or culturally knowledgeable. They scared me. I would hang up the phone and wonder whether the NSA whistleblower had been the first moral test for my generation of entrepreneurs and tech workers, and we had blown it.”

Wiener articulates her expanding ethical consciousness as mass surveillance becomes more apparent to her friends outside the tech industry. Watching non-technical people discuss their inklings about the surveillance industry leads Wiener to reflect on her own lack of concern when she worked at the analytics company. As this happens, the tone of the narrative darkens, and the weight of the industry’s invasion of private life—her own, and everyone’s—makes her uneasy.

“‘Do you think you hate yourself?’ asked a therapist in Berkeley. Coming on strong for an intake session, I thought, but the next day I caught myself following a bunch of venture capitalists on the microblogging platform. It wasn’t exactly an act of self-care.”

Though this question appears as humorous dialogue in a short scene, Wiener’s narration sidesteps the answer, allowing it to sit in the text rhetorically, igniting the reader’s curiosity about where she stands. She implies that her continuing fascination with and participation in the industry may be unhealthy or compulsive, less about self-respect than morbid curiosity. 

“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.”

The book’s final chapters signal a climactic character shift as Wiener finds language for a confident critique of the industry in which she has been a participant—or an accomplice—for too long. Many of these realizations grow from her awareness of social and political turmoil. Here, she connects to an anger and a disdain for how the “ecosystem” has been corporatized for entirely capitalistic ends. She laments that this talent and potential has not put itself to use in service of a more humanitarian or radical political goal.

“I was looking for stories; I should have seen a system. […] The person with the yearning was me.” 

Camping alone with Ian after Patrick’s birthday party, Wiener reckons with her tendency to empathize and assign deep needs and motivations to tech leaders and the powerful figures that surround her. In an important moment of character development, she sees that the needs and longings she imagined for CEOs and the like had little to do with them. She acknowledges that in searching for a narrative, she overlooked the reality of a system being built, fortified, and exploited for profit in front of her, and with her help.

“Women stood behind screen doors and looked at us, with our clipboards and patriotic stickers and aestheticized coastal corporate feminism, and simply shook their heads. At the curve of a cul-de-sac, in an affluent neighborhood of compact SUVs and ornate landscaping, we leaned against our rental car, bent over our phones. I unpinned the uterus and put it in my pocket. It had all seemed possible. It had seemed real. As if in slow motion, I felt the force of the swerve.”

Wiener experiences—and simultaneously represses—a profound sense of alienation in the final chapter as she attempts to canvass in Nevada before the Election Day. Once again, she sees herself through the eyes of others—this time, Nevadan women, uninterested in her political pitch. The detail of the uterus pin, an image of an organ outside the body meant to symbolize her feminism, seems dark and odd, and she conceals it. Rather than overcoming her alienation, she turns to her phone; the story ends on a somber, unsettled note, as Wiener describes a moment of suddenly sensing the political tectonic shift about to take place.