Inside Tech’s Fever Dream

Drawn into the tech world, a 20-something wonders why she—and the rest of us—didn’t wise up to the grandiose myopia sooner.

Chau Luong

Perhaps the most repeated phrase in Uncanny Valley, Anna Wiener’s memoir of life as a tech-industry worker, is “I did not know.” When the book opens, Wiener’s world feels like one with limited horizons. It’s 2013, and she’s a 20-something college graduate who has been working in the sclerotic New York publishing industry, stringing together a meager income as a freelance editor and an assistant at a boutique literary agency. “There was no room to grow, and after three years the voyeuristic thrill of answering someone else’s phone had worn thin,” she remembers in typically sardonic fashion. She’s not exactly poor, only “privileged and downwardly mobile.”

A new, more dynamic economy was taking shape on the other side of the country—“not that I was paying any attention,” Wiener writes. An unnamed “online superstore” known for its ruthless efficiency had elbowed its way into publishing and well beyond. “The social network everyone hated” was changing what it meant to be social. Venture capitalists were supporting these companies by shoveling billions of dollars at very young men who promised that their particular app would be the one to usher in a kinder, more connected world—while making its investors millionaires.

Though tech had insinuated itself into many facets of Wiener’s life—her waking hours were spent tethered to her computer, working, using the social network everyone hated, writing blog posts, and scrolling her way through images—she hadn’t stopped to think about the people, structures, and forces that had enabled that entwining. Then she got a tech job in San Francisco and discovered that the screens she had been staring at weren’t as transparent as they seemed. Yet she remained, by her own account, remarkably clueless about the larger implications of the industry she’d wandered into.

We’re not at a loss for in-depth accounts of the tech industry these days. Reporters, cultural critics, academic historians, and tech figures themselves have been busy trying to explain a social and economic paradigm shift that’s affected everything from our dating lives to the security of municipal infrastructure. Books like Alexandra Wolfe’s 2017 Valley of the Gods have fetishized Silicon Valley, offering portraits of tech as a culture apart, rising up to replace the moribund institutions that have failed society—academia, public transit, local news media, government. Other books, such as Zucked: Waking Up to the Facebook Catastrophe, by Roger McNamee, a venture capitalist and an early mentor of Mark Zuckerberg’s, have taken a far darker view. Where these accounts converge is in portraying tech as nothing less than the catalyst of a radically new social order.

Uncanny Valley is a different sort of Silicon Valley narrative, a literary-minded outsider’s insider account of an insulated world that isn’t as insular or distinctive as it and we assume. Wiener is our guide to a realm whose denizens have been as in thrall to a dizzying sense of momentum as consumers have been. Not unlike the rest of us, she learned, they have been distracted and self-deluded in embracing an ethos of efficiency, hyperproductivity, and seamless connectivity at any cost. Arrogant software developers, giddy investors, and exorbitantly paid employees—all have been chasing dreams of growth, profits, and personal wealth, without pausing to second-guess the feeling of being “on the glimmering edge of a brand-new world,” as Wiener puts it in the middle of her book.

Now, from the vantage of 2020, the unintended consequences of the chase are glaringly obvious. But why was the recognition so slow in coming? Wiener downsizes that question to human scale: How, even half a decade ago—a lifetime in the Valley—could everyone still have been so blinkered, from those at the top down to her and others at the bottom? Complicity is Wiener’s theme, and her method: She’s an acute observer of tech’s shortcomings, but she’s especially good at conveying the mind of a subject whose chief desire is to not know too much. Through her story, we begin to perceive how much tech owes its power, and the problems that come with it, to contented ignorance.

Wiener’s participant-observer journey calls to mind a predecessor. “I set out to write this book,” Michael Lewis explained 30 years ago in his now classic coming-of-age memoir cum exposé, Liar’s Poker: Rising Through the Wreckage on Wall Street, “because I thought it would be better to tell the story than to go on living the story.” Like Lewis, Wiener found “a way out of unhappiness” by writing her own gimlet-eyed generational portrait that doubles as a cautionary tale of systemic dysfunction. But if her chronicle acquires anything like the must-read status that Lewis’s antic tale of a Princeton art-history major’s stint at Salomon Brothers did, it will be for a different reason. For all her caustic insight and droll portraiture, Wiener is on an earnest quest likely to resonate with a public that has been sleepwalking through tech’s gradual reshaping of society. She’s interested in how an industry so invested in promoting a sense of community and “noble mission,” so brimming with assurance, left her feeling so dissociated from herself, so impotently eager to please, so uncurious about the world around her. Lewis gleefully made short shrift of the flagrant excess and dog-eat-dog allure of the finance sector of the 1980s, figuring that the youthful stampede into Wall Street had seen its heyday. Wending her way through the “promised land for millennial knowledge work,” as Wiener sums up the aura of Silicon Valley in the 2010s, is more disorienting.

Wiener’s swerve into tech took place in post-recession America, where even graduates from prestigious universities found the old economy’s wreckage jamming the path to wealth and power. “My desires were generic,” she offers by way of explaining her jump from publishing to tech. “I wanted to find my place in the world, and be independent, useful, and good. I wanted to make money, because I wanted to feel affirmed, confident, and valued.” Tech held out the opportunity to “feel like I was going somewhere,” to stop questioning her worth. In publishing, she writes, “nobody my age was excited about what might come next. Tech, by comparison, promised what so few industries or institutions could, at the time: a future.”

An article about an ebook start-up in New York attracted her interest. She interviewed for a job, and was hired in early 2013. It wasn’t a good fit—“She’s too interested in learning, not doing,” the CEO accidentally typed in the company-wide chat room—and she was soon fired. But Wiener had caught the bug. She landed a job as a customer-service associate at a thriving start-up in San Francisco that made a data-analysis tool. It was the hottest of products in an era when ever more finely articulated data about consumers had emerged as the most valuable commodity of all. After nearly two years of being “Down for the Cause”—as the young CEO demanded—she began to wonder about the psychological and social effects of tech, yet continued to drift through the Valley. Another support-team job, this one at an open-source start-up, meant a pay cut, but she was drawn by the promise of better work-life balance and the “idealism and old-school techno-utopianism.”

To watch Wiener watching herself become absorbed by her Valley existence, and then ever so gradually alienated, is to recognize along with her that the social life of the tech industry holds the key to understanding its hypnotic sway—and the corrosive effects of its cultlike culture. Paradoxically, the Valley’s vaunted commitment to transparency and social change gets in the way of perceiving its actual social effects. On Lewis’s every-man-for-himself Wall Street, brutal hierarchy, cutthroat drive, and greedy opportunism were out in the open. In the Valley, money still counts, of course: Billions of dollars slosh across the Bay Area. But Wiener was “seduced by the confidence of young men” who had recalibrated the style, and the scale, of ambition. These geniuses see themselves in direct competition with the “middle-aged leaders of industry.” Their own professed faith in principles that promise meaning and purpose, along with an “optimized” lifestyle, marks a crucial and contagious difference. Wiener bought into the narrative, trusting innovators who she thought would be enlightened versions of Wall Street titans. “I wanted to believe that as generations turned over, those coming into economic and political power would build a different, better, more expansive world,” she writes, “and not just for people like themselves.”

No wonder she let these men supply goals that felt suitably rewarding. Wiener is wittily merciless in portraying how susceptible she was to “the sense of ownership and belonging, the easy identity, the all-consuming feeling of affiliation” that start-up culture promotes. The quirky office camaraderie, the i am data driven T-shirts, the scavenger hunts, the CEO given to pronouncements like “We are making products … that can push the fold of mankind”—Wiener lets the details accrue. At this point, though, the self-parodic tech ambience is low-hanging fruit. Her real feat is exposing her own persistent failure to register the big picture. She had a ringside seat to just about every issue that has tarnished tech’s aura since 2016—privacy invasion, sexism, lack of diversity, internet harassment, conspiracy campaigns—yet she wasn’t especially attuned to trouble. She was too intent on making sure her bosses thought she was “smart and in control.”

At the analytics start-up, for example, Wiener came to understand that “transparency for the masses wasn’t ideal: better that the masses not see what companies in the data space had on them.” In fact, she experienced the allure of unfettered access to data herself. In order to solve her customers’ problems, she was permitted to use a setting known as “God Mode,” which let her see customers’ data on their customers, as if invading privacy were a video game. “Data sets were mesmerizing,” she confesses. And when a government whistle-blower revealed that just this sort of information could be accessed by intelligence services, her supervisor was quick to rally employees to the Cause. “Don’t forget, we’re on the right side of things,” he told them. “We’re the good guys.”

“For all the industry’s talk about scale, and changing the world, I was not thinking about the broader implications,” Wiener writes. “I was hardly thinking about the world at all.” She’d exchanged cluelessness about what was behind the internet for willful ignorance about the tech industry’s impact on the world. But Millennial that she is—a beneficiary, she wryly notes, of “two decades of educational affirmation, parental encouragement, socioeconomic privilege, and generational mythology”—she finally began to see the toll the industry was taking on her.

Tech’s ethos of optimization, far from giving her genuine purpose, had sent her—in her job and in her life—careening “across the internet like a drunk.” Meanwhile, beyond the Valley, America was roiling, its polarization intensified by social media, and digital surveillance was spreading—not that Wiener really noticed. “I had felt unassailable behind the walls of power. Society was shifting, and I felt safer … inside the machine.” The 2016 election jolted her. In succumbing to the “overwhelming myopia” that had served to entrench tech and leave inequities untouched, she realized she had company. “An entire culture … had been seduced” by faith in efficiency and easy connectivity, by an empty promise of momentum and mission.

Looking back at Liar’s Poker in 2011, Lewis remarked that he had “thought it was about a period that was coming to an end. I thought a system that paid a 24-year-old like me to give financial advice must be crazy, but I never thought it would last.” Wiener found herself in a similar position after the election. “I thought, for a while, that everything would change. I thought that the party was over.” She anticipated a newly chastened Valley, forced into an awareness of its deficiencies and shorn of its excesses. But like Tom Wolfe’s Masters of the Universe, the young men of Silicon Valley weren’t interested in humility. “They had inexorable faith in their own ideas and their own potential,” she says. The election only marked a new cycle in tech’s life span, a new chance for its titans to prove their exceptionality. At an industry event, a fellow tech employee confided to Wiener: “We’re the government now.” In the Valley, the new Masters of the Universe are still dreaming, and Wiener has no illusions that they will wake up.

This article appears in the January/February 2020 print edition with the headline “The View From Inside the Bubble.”