Part of the uncanniness of Uncanny Valley, Anna Wiener’s memoir of her time at a series of tech startups, is its familiarity. As a vivisection of tech’s bleak buoyancy, the internet’s death grip on our lives, and the hideous, misplaced confidence of the people who design and run these systems, it’s essential reading. But the book is also about the idea of work: the weight of it; its ideals, temptations, and contradictions; the seduction of a paycheck and a promotion; the dynamic of a team; the struggle to understand what makes something a job or a career or a calling, and where the lines are between those things. More than the timely (and entertaining) expose of a sick industry, it’s the broader job stuff that sent me reeling.

Wiener starts out as a low-level employee in publishing, a field rich in cultural capital but lacking things like decent pay and a shot at upward mobility. When she takes a job at an e-book startup, it seems like a savvy pivot, one that doesn’t force her to compromise her interests or her talent. But after her assigned duties and personal motivation both prove too ambiguous to be sustainable in that context, it doesn’t take much urging for her to turn away from publishing entirely and parlay her new tech-adjacent experience into a job working in customer support at an analytics startup in Silicon Valley. Though she wasn’t exactly successful at her first startup job, she was seduced by her brief encounter with the tech sector’s “optimism and sense of possibility”—its innate belief that it makes sense to be excited about the future.

It’s a decision she struggles to explain to her New York friends, who trend “countercultural and creative” and largely suspicious of tech. The narrative she develops to reassure them (and herself) includes the notion that “Working in analytics would be an experiment in separating my professional life from my personal interests.” In said experiment, she’ll have the chance to see what it’s like to have “just a day job,” employment that doesn’t feel synonymous with her soul and self-worth. The learning curve is steep, but Wiener is happy: “For the first time in my professional life, I was not responsible for making anyone’s coffee. Instead, I was solving problems.” She learns about cookie tracking, how to navigate code, how to troubleshoot issues with product integration. She begins to orient herself in this strange and not-so-brave new world, where big data is fetishized, baby-faced founders are lionized, and the average tech worker has at their disposal reams of data tracking your every click and craving—and in a city that earnestly preaches “affluent idealism,” comes face-to-face with poverty and misery, then looks the other way.

Workplaces are weird, regimented and clubby, filled with people mashed together more or less by chance, oriented to a common goal (at least officially), the office inhaling and exhaling at the pace of the conference room sign-up. Your coworkers’ eccentricities take the form of conspicuous ergonomic preferences, yellowing cartoons tacked up next to open-plan desks, and the compost heap in the back of the communal fridge. The aesthetics of startup culture, in particular, have always seemed a little like the stuff of fiction, in-jokes or pipe dreams brought to life by an influx of cash and delirium. The effect is cartoonish, dreamlike, just on the border of believable.

So it’s fitting that over the past decade they have been the setting and inspiration for some especially absorbing, unsettling fiction. From Joshua Ferris’s And Then We Came to The End and Ed Park’s Personal Days to the more recent Severance by Ling Ma and the forthcoming, excellent Temporary by Hilary Leichter, writers have seized on the sense (or experience) of offices as surreal places, using them to build narratives that become more outwardly strange. (In a New York City office tower, the protagonist of Severance is preoccupied by the logistics of getting bedazzled Bibles produced in China—and then suddenly things are very wrong, with a deadly flu turning everyone into zombies.)

* * *

While there are no zombies in Silicon Valley, at least not literal ones, Wiener is still pretty naïve about what she’s walking into. The list of things she isn’t prepared for, or doesn’t know, is long (“that three million dollars is considered a modest fundraising round,” that “cheerful determination” could compensate for a lack of traditional qualifications, “that equity was an option”), and the same is true of the lifestyle she’s adopting (how “the home-sharing platform” she availed herself of when she relocated was affecting the local community, her company’s “role in facilitating and normalizing the creation of unregulated, privately held databases on human behavior”). In hindsight, she owns her blind spots. In many ways they are the foundation of her story, and a point of connection with us outsiders.

She also lists what she does know, has always known, and firmly believes: what she wants when it comes to work. “I wanted to find my place in the world, and be independent, and useful, and good. I wanted to make money, because I wanted to feel affirmed, confident, and valued. I wanted to be taken seriously. Mostly, I didn’t want anyone to worry about me,” she writes early on, considering whether to accept an offer from the e-book startup. Not long after, reflecting on her interview with the analytics startup: “I wanted to impress. I wanted to be taken seriously.” And later, after she’s been with that company for awhile: “I wanted the men to think I was smart and in control…. I wanted them to see me as an equal.”

As I underlined these sentences, I was struck by their recurrence and prominence, and the ways that they, together, amounted to a kind of manifesto. Or a plea. It was poignant, her careful effort to lay out what she wanted from a job, stripping it down to the essentials without setting the bar too high. Money. Dignity. Fairness. A cause. On paper, these things seem reasonable, achievable! Wiener doesn’t think she’s asking too much. But companies have a way of creating their own realities.

The reality developed by the analytics startup is given structure by a cultish insistence on being “Down for the Cause” (invoked regularly, menacingly, as “DFTC”). In explaining DFTC, and trying to unpack what “the cause” actually is, Wiener points at first to on-the-record goals like optimizing productivity, increasing click-throughs, and improving efficiency—basic metrics that might be assessed in a performance review. But the real “cause,” which is never explicitly stated by the company but rapidly becomes very clear, is much bigger than that. It is, in her words, the vision of “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. A world freed of decision-making.” It’s a world Wiener recognizes as distinctly at odds with the one that she prefers, brightened by “banal inefficiencies” and unstructured, even wasted, time. So no, she’s not down. But her survival requires that she pretend otherwise, and the line she’d tried to draw between personal and professional begins to blur.

“What I wanted in a workplace was simple,” Wiener writes. “I wanted to trust my manager. To receive fair and equal compensation. To not feel weirdly bullied by a twenty-five-year-old. To put some faith in a system—any system would do—for accountability. To take it all much less personally, and not get too close.” By this point she has burned out on the particular psychodrama of the analytics firm and its cause, and is on the hunt again. “I just wanted to work for a company that was innovative, rather than opportunistic, with a stable revenue model and a mission I could get behind.” She gets an offer from a company promising higher principles and a better work-life balance, a title demotion, and a pay cut, and she takes it.

She refers to the company as “the open-source startup” (all the companies in the book have these generalized descriptions but are pretty easily identifiable, this one as GitHub), and initially it seems to fit the bill. But with more time and space to think, there is somehow less room for purpose, and more for ennui. Wiener is paid well; she works mostly from home and has attained the holy grail of flexibility. Her job is pretty easy and entirely online, and no one is really looking over her shoulder—unusual in an industry where it’s understood you should be working all the time, and furthermore should want to. (One day Wiener’s boyfriend, an engineer who works in robotics, jokes that the two of them should split her job, so they can both work part-time and travel: “Who would ever know?”) Instead of freeing her up, though, the luxuries of the job make her numb.

In the thick of Silicon Valley self-improvement culture, the list of what Wiener desires inevitably extends to what she wants of herself, too. “I wanted to be more open and thoughtful, more attentive and available…. I wanted to stop hiding discomfort, sadness, and anger behind humor. I wanted a therapist to laugh at my jokes and tell me I was well-adjusted. I wanted to better understand my own desires, what I wanted; to find a purpose.” There it is again, “a purpose,” though this time at the end of a list not about the qualities of work, but of self. Through all the pressure to be a particular kind of person, a particular kind of worker, a particular kind of woman, Wiener writes, “I still wanted to be a part of something.”

* * *

After they have some back and forth on Twitter, Wiener strikes up an unlikely friendship with the young CEO of a prominent company. Over lunch, she tries to explain to him why the book reviews she’s writing on the side could never be a “real job.” Partly, she says, it’s because she needs health insurance. It’s also because she doesn’t really know what she wants to do, what her goals are, and therefore what it would entail to pursue them, so she broadens her lens: “I wanted work to be intellectually engaging, and I wanted to do it alongside smart, curious people. I wanted long-term projects. I wanted it to matter.” After that, they sit in silence, Wiener’s “directionlessness” heavy in the air, an awkward contrast with her new friend’s status as a founder, and whose life presumably has plenty of direction.

Who among us does not want the things Wiener does? I did; I do. What I don’t know anymore is how reasonable is it to try to find them in a job. Like Wiener, I grew up being told, and so believing, that my goal (and to some extent my purpose) was to find satisfying, meaningful work, something that aligned with my interests and principles and thus amounted to “a good fit.” As I ventured into the professional world, I quickly saw that there were the specific tasks of a job, and there was the place you did them in service of. If you felt good about the latter, it could be okay to feel unenthusiastic about the former. The ultimate goal, something approaching the definition of a “dream job,” was to feel excited about both the company or organization and the actual work itself. Presumably, that would happen as you gained experience, moved up, got more opportunity and visibility.

I wanted to work in journalism, and graduated with my master’s degree just before the 2008 recession. I had one staff job in media, and was laid off soon after Obama was inaugurated. In my un/underemployment, I enthusiastically wrote book reviews for paltry sums, many for publications that no longer cover books, or even exist. Eventually, my early experience working in nonprofit communications—courtesy of an assistant job I had taken when I didn’t get any interviews for the entry-level publishing positions I applied to after college—proved more valuable to my employment prospects than my new advanced degree, or my genuine love for the collapsing industry I badly wanted to be a part of.

When I got my most recent nonprofit comms job, I was filled with a sense of relief not unlike being in a committed, long-term relationship. I could settle in, get comfortable. Until I heard myself saying it, that wasn’t something I’d ever thought I wanted. The job was seductive in the abstract; the work was in my wheelhouse and the organization carried a general whiff of prestige. It was a place with good values, with a familiar name and self-explanatory mission. This was, decidedly, not a tech job.

Like Wiener, I took it, and like Wiener, it didn’t take long for me to feel stuck and disillusioned. The organization was Doing Good Things, probably, but the work I was doing ostensibly in support of that good felt too many layers removed, smothered by bureaucracy and circular discussions of strategy and a near-pathological aversion to risk. I was frustrated, angry and yet listless. But I was paying my rent. I got promoted. I bought nice clothes, too many of them, out of boredom and an embarrassingly transparent attempt to fill the void. I went out to dinner and was generous with my friends and donated money to causes I cared about. I wrote when I could, and I told myself I should be writing more, taking advantage of my situation. This was a Good Job. I was lucky. It was a ridiculous privilege to be able to worry about work in the context of idealism, as opposed to survival. But I was tired and often short-tempered, caught between wanting my job to feel purposeful and being fine with the fact that it wasn’t—something made more difficult when the people around me kept insisting that it was.

All of this was on my mind when I read Uncanny Valley, which I did on a plane, half on the way out; half on the way back, in the liminal state between home and away. I was on vacation; I was not working. In fact, I did not have a job to return to. The sense that this was something I wanted, needed even, had come on slowly, but the feeling was persistent, and then it happened all at once.

In that mode, I reread Anne Helen Peterson’s essay on millennial burnout, published on BuzzFeed about a year ago. Digging into the roots of this particular strain of existential exhaustion and frustration, Peterson lit up the internet—people shared their own stories of deep fatigue and overwhelm, disappointments and breakdowns. (Of course there was also some backlash, as happens—perhaps unavoidably and in many ways understandably—whenever anyone openly discusses the particular strains of millennial existence.) Peterson argued that this generation grew up understanding that their ultimate goal was to secure “1) a ‘good’ job that would 2) be or sound cool and 3) allow me to follow my ‘passion.’” Broken down like that, it sounds like a tall order, especially alongside the grim realities of crushing student debt, the gig economy, and this country’s profound failure to provide even basic healthcare and family leave. Increasingly, the synthesis of Peterson’s three factors looks like a fantasy, a genuine dream job.

Still, we want it badly. We believe in it. Wiener wanted it, and so did I, and in the arc of her disillusionment I saw my own. It is easy, and satisfying, to dismiss the excess and hypocrisies of Silicon Valley—when so much of it is couched in cultish nonsense and self-important zealotry, how can we resist? But in her careful attention to the particularly uncanny world of tech, Wiener’s trick is in showing that we’re all implicated—in the systems we use to distract ourselves, as well as in the ways we manage our lives and greater ambitions. She doesn’t offer any career advice; her enviably happy ending involved writing a memoir and securing a perch at The New Yorker. But Wiener shrewdly suggests that to feel smug and laugh too loudly at the Silicon Valley set is to ignore the myriad ways that we are the butt of our own joke.

Eryn Loeb

Eryn Loeb is deputy editor of Guernica. Her writing has appeared in The Los Angeles TimesLongreads, Bookforum, Poets & WritersThe Awl, and other publications.

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