
Uncanny Valley
A Memoir
Categories
Business, Nonfiction, Science, Biography, Memoir, Technology, Audiobook, Feminism, Biography Memoir, Book Club
Content Type
Book
Binding
Audible Audio
Year
2020
Publisher
Fourth Estate
Language
English
ASIN
B08253CZ7C
File Download
PDF | EPUB
Uncanny Valley Plot Summary
Introduction
As the sun set over San Francisco Bay, painting the iconic skyline in hues of gold and amber, a young woman stood at the crossroads of her career. Behind her lay the comfortable familiarity of the publishing world—literary agency meetings, manuscript reviews, and the quiet dignity of words on paper. Ahead stretched the gleaming promise of Silicon Valley—a land of unicorns, venture capital, and twenty-somethings certain they were changing the world. With a mixture of curiosity and trepidation, she stepped into this new realm, not realizing how profoundly it would transform her understanding of power, technology, and herself. This narrative unfolds at the intersection of two worlds—the traditional intellectual economy and the emerging digital one. Through an immersive journey into startup culture, we witness how technology has fundamentally altered not just our economy but our very identities. The personal story of adaptation and disillusionment serves as a lens through which we can examine larger questions about modern work, surveillance capitalism, and the meaning we derive from our professional lives. As the digital revolution continues to reshape society, this insider's account offers valuable insight into the promises and perils of the tech industry's outsized influence on our collective future.
Chapter 1: The Outsider's Gaze: From Publishing to Tech
The literary agency office hummed with a familiar energy—editors' calls, manuscript deliveries, the quiet rustle of paper. At twenty-five, with three years in publishing behind her, the narrator found herself at a turning point. Her salary barely covered rent in Brooklyn, and the career path ahead seemed to lead only to more of the same—answering someone else's phone, filing contracts into desk drawers, and proofreading manuscripts for a small press. When news crossed her desk about a startup raising three million dollars to "revolutionize" book publishing through an e-reading subscription app, she was both skeptical and intrigued. "Would a subscription model undercut author royalties?" her publishing friends later challenged when she announced her decision to join the e-book startup. "Wasn't it basically a cynical, capitalist appropriation of the public library system?" These were questions she didn't have good answers for, but the prospect of making $40,000 a year—a substantial jump from her $30,000 literary agency salary—and stepping into the buzzing tech ecosystem proved irresistible. The three young co-founders, all younger than she was, exuded a confidence and certainty about the future that she found magnetic. Her first weeks in the tech startup revealed a different world. The office was a spare table in a loftlike space belonging to a more established startup, where pour-over coffee vessels and local roaster beans lined the kitchen counter. The team consisted of just the three founders and one mobile engineer. They spoke in a language of metrics, user engagement, and scalability that made her publishing vocabulary feel quaint. She was handed books about technology and invited to team-building exercises—field trips to libraries and museums, activities that blended work and leisure in ways that publishing never had. Yet she soon discovered that the tech world expected her to create her own path without instruction. "She's too interested in learning, not doing," the CEO typed into the company chat room, accidentally including her. The implicit expectation was that she would hustle, take ownership, and make herself indispensable—qualities that weren't necessarily rewarded in her previous professional life. When she failed to adapt quickly enough, the founders gently suggested it wasn't the right moment for someone like her to "get up to speed." As she contemplated her return to publishing, she realized something had shifted. The tech industry had shown her a world of optimism, open-mindedness, and possibility—a sense that the future was being actively built, not passively received. When the co-founders offered to help find her another tech job, she accepted their guidance rather than retreating to the familiar. The industry had spoiled her with its speed and sense of possibility—what other field promised a future to young people in a post-recession economy? This first glimpse of Silicon Valley's promised land, even in its New York satellite office, had awakened an appetite for more.
Chapter 2: The Culture Code: Adapting to Silicon Valley
The analytics startup interview in San Francisco was unlike anything she had experienced. Instead of professional conversation, she faced a bizarre gauntlet of brainteasers: calculating postal service employee numbers, explaining the internet to medieval farmers, and strangely, taking a section of the LSAT while a technical co-founder checked his email. The office was massive but sparsely furnished, with about fifteen employees clustered at one end, some standing at elevated desks on rubber mats. Far from the buttoned-up publishing interviews, here she felt overdressed in her shift and blazer among employees in jeans, sneakers, and company t-shirts declaring "I AM DATA DRIVEN." Despite the disorienting interview, she received an offer: $65,000 annually, medical benefits, and a relocation stipend. When an in-house recruiter suggested she should negotiate for equity, she didn't even understand what that meant—no one explained its value or how much was standard. This knowledge gap foreshadowed many cultural differences she would encounter in Silicon Valley, where unwritten rules governed success and failure. Her first days as employee number twenty revealed an alien landscape where coworkers zipped around the office on RipStiks, drank energy shots, and spoke a language peppered with technical jargon. Survival required adaptation. She began wearing flannel shirts and work boots, incorporating B vitamins into her regimen, and listening to EDM while working. The music gave her "delusions of grandeur," making her wonder: "Was this what it felt like to hurtle through the world in a state of pure confidence—was this what it was like to be a man?" She learned to speak confidently about cookies, data mapping, and server-side versus client-side implementation without fully understanding the technology. When customers complained that the analytics software wasn't working, she reassured them that their implementation was at fault, not the product, which was "never broken." The office culture revolved around camaraderie, long hours, and devotion to company growth. "We were the company; the company was us," she observed. Everyone stayed close physically and emotionally—they knew who was hungover, who suffered from stress-induced IBS. They judged each other by the "ass-in-chair metric," their presence proof of commitment. Slacking off wasn't an option; if someone was missing, something was wrong. The CEO fostered this intensity, speaking in military terms during weekly all-hands meetings: "We are at war," he would say, standing before them with crossed arms. "We are at war with competitors, for market share." As she integrated into this culture, she found its rewards intoxicating: the salary increases, the sense of belonging, the shared mission. Yet something fundamental was changing in her identity. The tech industry was becoming not just where she worked, but who she was becoming—a transformation that began with clothes and music but would soon extend much deeper, reshaping her values, priorities, and relationship to the world around her. Silicon Valley's culture wasn't just something to navigate; it was something that navigated her.
Chapter 3: Gods and Mortals: Power Dynamics in Startups
The first time she saw God Mode, she understood something essential about Silicon Valley's power structure. As a customer support engineer at the analytics startup, she gained access to all their customers' data sets—seeing the tool "as if we were logged in to any given user's account." This meant watching every click, tap, and interaction across countless apps and websites. "We're not just selling jeans to miners," her coworker Noah explained. "We're doing everyone's laundry." Through this privileged vantage point, she observed startups rumored to be "rocket ships" sputtering to get off the ground, gaming apps spiking and flaming out within weeks, and companies with breathless tech-blog coverage quietly failing. "It was assumed we wouldn't look up individual profiles of our lovers and family members," she writes. "It was assumed we wouldn't check back on past employers to see how they were faring without us." With no formal policy against insider trading, the small company of twentysomethings operated on good faith, even as they held the power to see which public companies were thriving or failing based on user data—information that could easily inform stock purchases. The company's unofficial motto—"Down for the Cause" (DFTC)—fostered intense loyalty, with employees desperate for the CEO's rare approval. This power imbalance extended beyond customer relationships. At the analytics startup, non-engineers constantly had to prove their value. The hierarchy was pervasive in the CEO's dismissal of marketing and his insistence that "a good product would sell itself." It was reflected in salaries and equity allotment. Despite evidence that emotional intelligence couldn't be taught, unlike programming languages, soft skills were undervalued. The operations manager—who ran payroll, planned events, worked as a technical recruiter, designed the interior, assisted the CEO, and served as ad hoc HR—was paid less than engineers who could "teach themselves to code over the summer." At team-building events, these dynamics intensified. During the annual ski trip to Tahoe, the CEO announced that engineers would handle customer support to "allow the support team leisure time." While this initially felt like a power reversal, she later realized the implication: "our job was so easy, anyone could do it. They could even do it drunk." In the hot tub, she overheard the solutions manager asking a support engineer about his tattoos, knowing this engineer desperately wanted whatever leadership role she held. "I knew that he would get it," she observed, pinpointing how power was already shifting beneath the surface. These experiences revealed Silicon Valley's core contradictions: a culture that preached meritocracy while reinforcing privilege, that celebrated disruption while preserving hierarchies, that promised liberation while creating new forms of control. Power wasn't just about who had the most stock options or sat closest to the CEO—it was about who controlled the data, who determined the metrics of success, and who decided which skills were valuable. In this world of gods and mortals, even those with access to divine powers remained subject to the capricious judgments of those above them.
Chapter 4: The Growth Machine: When Numbers Rule
"Our culture is dying," she and her coworkers would say gravely while toasting bagels in the company kitchen. The analytics startup was growing rapidly, with new salespeople flooding in: "well-groomed social animals with good posture and dress shoes, men who chuckled and smoothed their hair back when they couldn't connect to our VPN." After nearly three years of explosive growth, the once-intimate startup was transforming into something unrecognizable. Their desks were scattered with freebies from customers—stickers, beer sleeves, flash drives—while rumors circulated that their base salaries were twice what support engineers made. They'd chosen cash over equity, making them untrustworthy in the eyes of early employees. The once-flat organization was developing layers. The CEO began using the word "paranoid" frequently, and their primary investor had funded a direct competitor. Fear spread that they'd been "hiring their own replacements all along." Yet the weeks ticked by without incident, and every Tuesday afternoon, the emergency warning siren heralded good news about revenue, investors, and valuation. The company's growth graphs "looked like cartoons of revenue graphs," and engineers had built an internal website where employees could watch money come in real-time. The message was intoxicating: "Society valued our contributions and, by extension, us." This growth mindset permeated the entire industry. The startup had released a feature called "Addiction" that displayed how frequently individual users engaged with apps on an hourly basis. "Addiction allows companies to see how embedded they are into people's daily lives," she wrote in promotional materials, as if this were unequivocally positive. When she expressed discomfort with the name to a coworker, he reminded her: "We already call our customers 'users.'" The industry's language revealed its priorities—growth at any cost, engagement above all else. Even as her role expanded to "Customer Success Manager" with a salary of $90,000, she began questioning the machine she served. The end goal seemed to be "a world improved by companies improved by data. A world of actionable metrics, in which developers would never stop optimizing and users would never stop looking at their screens." The system was working toward "a world freed of decision-making, the unnecessary friction of human behavior, where everything—whittled down to the fastest, simplest, sleekest version of itself—could be optimized, prioritized, monetized, and controlled." This growth-at-all-costs mentality was reshaping not just companies but human behavior itself. Metrics became the only reality that mattered, with the human elements—creativity, intuition, ethical concerns—dismissed as inefficiencies to be eliminated. What began as a tool for understanding user behavior had evolved into an architecture for reshaping it. The very systems that promised freedom through technology were quietly constructing a world where humans served the machine, not the other way around. For those inside the growth machine, the only direction was forward, faster—even if no one could articulate where exactly they were racing toward.
Chapter 5: The Ethical Void: Data, Surveillance and Responsibility
In midsummer, news broke that an NSA contractor had leaked classified information about the U.S. government's massive surveillance programs. The analytics startup employees ignored the push notifications, debating instead where to grab takeout: "the food court of the mall down the block, or the Mexican place?" They returned with passable Thai food and high-sodium ramen, talking about podcasts and weekend plans. None of them discussed the whistleblower, even during happy hour. "We weren't thinking about our role in facilitating and normalizing the creation of unregulated, privately held databases on human behavior," she reflects. "We were just allowing product managers to run better A/B tests." The single moral quandary they acknowledged was whether to sell data to advertisers—which they didn't do, making them "righteous about it." The solutions manager would reassure them: "Don't forget, we're on the right side of things. We're the good guys." But this self-perception became harder to maintain as she moved to the open-source startup and joined the Terms of Service team, where she confronted increasingly disturbing content: revenge porn, child pornography, terrorist content, phishing sites, suicide notes, malware, and conspiracy theories. Four employees handled nine million users, making moderation decisions with no clear guidelines. "We wanted to be on the side of human rights, free speech and free expression, creativity and equality," she writes. But the team struggled to draw lines between political acts and views, between praise of violent people and praise of violence itself. "We tried to distinguish between commentary and intention. We tried to decipher trolls' tactical irony. We made mistakes." The mostly white, North American team in their twenties and thirties was painfully aware of their blind spots, but these remained blind spots nonetheless. Even pornography required context: "An artistic photograph of a woman breastfeeding was not the same as an avatar of an anime character spouting milk from physiologically untenable breasts. But what was art, anyway, and who were we to define it?" For safety reasons, she began using male pseudonyms for all external correspondence. This wasn't just for sensitive situations—it worked better for routine inquiries too. "Men, I saw, simply responded differently to men. My male pseudonyms had more authority than I did." Meanwhile, disturbing harassment campaigns targeted women in tech and gaming. When a far-right publication attacked the VP of Social Impact, menacing vitriol spread across social media. Some threats were specific enough that the company hired security escorts. A threatening note appeared on the employee entrance door. Looking back on this period, she realizes the whistleblower had presented "the first moral test for my generation of entrepreneurs and tech workers, and we had blown it." The ethical void wasn't just about the lack of formal policies—it was about the industry's fundamental unwillingness to acknowledge its responsibilities. Technology companies had built powerful tools for surveillance, data collection, and behavioral manipulation, yet refused to see themselves as anything but neutral platforms. When friends outside the industry would text, suspicious about ads for groceries they had just purchased, she felt like a sociopath when she tried to explain. "These conversations didn't make me feel superior or culturally knowledgeable. They scared me. I would look across the table into the confused faces of smart, hopeful, well-informed participants in civil society, and think, with dismay: They really don't know."
Chapter 6: The Human Element: Finding Identity Amid Technology
Her apartment in the Haight district of San Francisco became a front-row seat to the city's painful contradictions. The historic neighborhood that had incubated sixties counterculture now served as a crash course in societal neglect. Outside her window, people gathered on the corner, "playing guitar, picking fights, and hawking drugs," while tourists wandered the main drag taking photographs of murals depicting long-dead musicians. "At sundown, in the doorways of stores selling tie-dye leggings and postcards of acid pioneers, people curled up in secondhand camping gear and atop cardboard boxes," she writes. "It was possible that the tourists trawling the commercial strip mistook San Francisco's homelessness epidemic for part of the hippie aesthetic." Working remotely from this setting created a strange dissociation. Clocking in felt like "entering a tunnel," as she dropped emojis into team chat rooms, processed copyright takedowns, and skimmed internal message boards. After completing these cycles, she would "open a new browser window and begin the day's true work: toggling between tabs." Her internet browsing became a compulsive vortex: "small-space decoration ideas; author interviews; videos of cake frosting; Renaissance paintings with feminist captions. Cats eating lemons. Ducks eating peas." She found herself examining strangers' acai bowls, watching abdominal workout routines, and zooming in on photographs of wine cellars in Aspen. "My brain had become a trash vortex, representations upon representations." This digital immersion wasn't unique to her. Everyone she knew was "stuck in a feedback loop with themselves," while technology companies stood ready to "become everyone's library, memory, personality." The algorithms showed her New York friends hanging out without her, beautiful women making candy and throwing pots, and B-list actors "getting centered in Iceland." Yet the platforms also revealed darker elements: amber alerts hovered above notices about package theft, corporate acknowledgments of terrorist attacks appeared between discussions of reality television and chicken thigh recipes. "Everything was simultaneously happening in real time and preserved for posterity, in perpetuity." Even amid this digital deluge, she sought human connection. She began dating Ian, a software engineer who worked at a small robotics studio later acquired by the search-engine giant. Unlike her, Ian had a skill set that was "neither unique nor in high demand." He could "easily command three times my salary," and "no company would ever neglect to offer him equity." Yet he was humble and present, refusing to talk about his work at parties and maintaining strict boundaries between his personal and professional identities. Their relationship offered her glimpses of an alternative relationship to technology—one grounded in the physical world and meaningful connection. At a rave in the Sacramento Delta, she observed how even counterculture was being absorbed by startup culture. With reluctance, Noah and Ian's friends began moving into the tech industry: "a principal at a public elementary school took a job at an education startup making scheduling software. A music critic wrote copy about fitness and meditation apps." Everyone needed a hustle as artists, musicians, and public servants left San Francisco. Even the cuddle therapist at the rave asked Ian about coding boot camps. This commercialization of alternative lifestyles felt like "a performance from an imperfect past, a reenactment" rather than authentic liberation. As she negotiated these contradictions, she realized that "technology was gnawing into relationships, community, identity, the commons." The very devices and platforms promising connection were subtly undermining it. Her search for meaning amid the digital noise reflected a broader human yearning—to be present, embodied, and connected in ways that technology simultaneously enabled and eroded. This tension between digital and physical existence, between algorithmic and human identity, became the central struggle of her Silicon Valley journey.
Chapter 7: Disillusionment: When the Bubble Begins to Burst
The turning point came unexpectedly. One afternoon, she received an instant message from the CEO of the analytics startup, offering her a position doing content marketing. "I'd been interested in it before," he noted, adding, "I thought I'd see if perhaps you were still in love with the idea." The word "love" lingered—a calculated emotional hook. Despite Ian's reminder that "last time you did content, they didn't want to pay you for it," she found herself tempted by the opportunity to "overwrite my own feelings of failure" and prove she belonged. This pattern of seeking validation from tech had become deeply ingrained. She had spent years studying the industry's power brokers, particularly venture capitalists who dominated social media with their opinions on everything from universal basic income to whether nations could be startups. "I couldn't imagine making millions of dollars every year, then choosing to spend my time stirring shit on social media," she observed. Yet she couldn't look away, recognizing these posts as "the raw male id of the industry," revealing "the deliberately amplified identities, ideologies, and investment strategies of the people transforming society—the people I was helping make rich." The disillusionment accelerated during the 2016 presidential election. Along with friends, she traveled to Nevada to canvass, wearing an enamel pin shaped like a uterus and feeling certain of victory. Her social media feeds overflowed with feminist slogans and iconography, creating a false sense of consensus. The shock came when women in Nevada suburbs "stood behind screen doors and looked at us, with our clipboards and patriotic stickers and aestheticized coastal corporate feminism, and simply shook their heads." As realization dawned, she "felt the force of the swerve." After the election, tech's response was predictably self-centered. On the heavily moderated message board, the commentariat discussed "a Marshall Plan of rationality," while a sales leader suggested "crowdfunding private planes to fly over red counties and drop leaflets with facts about the travel ban." Their solution, as always: more technology. CEOs and venture capitalists extended olive branches to elected officials, while advocating primarily for immigrants who knew how to code. At a gathering of content moderators, a high-level employee of a household-name startup approached her with a startling claim: "There are no adults in the White House. We're the government now." When the open-source startup was purchased for $7.5 billion, making many of her former coworkers millionaires and the founders billionaires, her feelings were mixed. The shares she had exercised were worth about $200,000 before taxes—"a windfall by my standards, if modest for the industry." She felt "no pride, only relief and guilt," especially knowing that some coworkers, "largely women in nontechnical roles whose work had been foundational to the company," had been unable to exercise their options due to low salaries. "Flat structure, meritocracy, non-nonnegotiable offers. Systems do work as designed," she concluded bitterly. Walking through the Mission one day, she spotted the analytics startup's former CEO sitting outside a fast-casual Greek restaurant. "Nearly five years had passed, but I recognized him immediately: gelled hair, slight frame, green jacket. He looked happy, relaxed, older. He looked just like anyone else." Rather than engage, she "turned and walked as quickly as possible in the opposite direction," confident he never saw her. This brief encounter crystallized her journey—from eager acolyte to disillusioned exile, from someone who once desperately sought his approval to someone who now chose to walk away. The bubble hadn't burst for Silicon Valley, but it had for her.
Summary
Silicon Valley's promise seduced a generation with its intoxicating blend of wealth, purpose, and power. The journey from outside observer to industry participant reveals how easily we can be drawn into systems that reshape not just our careers but our identities. Through immersion in startup culture—from God Mode data access to the cult-like "Down for the Cause" mentality—we witness how technology's influence extends far beyond products and platforms. It fundamentally alters how we perceive ourselves, our worth, and our relationship to the world around us. What remains when the startup fever breaks is a profound reckoning with values. The tech industry's growth-at-all-costs ethos, its ethical blind spots, and its concentration of power force us to question what truly matters. Perhaps the most valuable insight is recognizing that our worth isn't determined by metrics, equity, or proximity to Silicon Valley's power centers. The human elements that tech culture often dismisses as inefficiencies—reflection, doubt, ethical consideration—are precisely what enable us to resist being reduced to data points in someone else's growth curve. As technology continues reshaping society, maintaining our humanity may be the most revolutionary act of all. The true disruption isn't in the next unicorn startup but in reclaiming our agency amid the machines we've built to serve us.
Best Quote
“Sometimes I would worry about my internet habits and force myself awy from the computer, to read a magazine or book. Contemporary literature offered no respite: I would find the prose cluttered with data points, tenuous historical connections, detail so finely tuned it could have only been extracted from a feverish night of search-engine queries. Aphorisms were in; authors were wired. I would pick up books that had been heavily documented on social media, only to find that the books themselves had a curatorial affect: beautiful descriptions of little substance, arranged in elegant vignettes—gestural text, the equivalent of a rumpled linen bedsheet or a bunch of dahlias placed just so. Oh, I would think, turning the page. This author is addicted to the internet, too.” ― Anna Wiener, Uncanny Valley
Review Summary
Strengths: The reviewer acknowledges that Wiener is a very good writer with a sharp wit and some good turns of phrase. The original essay that inspired the book was also appreciated.\nWeaknesses: The book is criticized for feeling like an extended long-form essay with little narrative arc. The reviewer felt a lack of investment in the narrator and the broader world depicted. Subplots were seen as underdeveloped or muted. Characters were reduced to tech bro archetypes without exploring their underlying psychology. The book lacked nuance, resembling a caricature rather than a deep exploration.\nOverall Sentiment: Critical\nKey Takeaway: While Wiener demonstrates strong writing skills, the book falls short in narrative development and depth, offering a surface-level critique of the tech world without delving into the complexities of its characters or ecosystem.
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Uncanny Valley
By Anna Wiener









