Be "Down for the Cause. DFTC." This was the mandate to employees at the startup Anna Wiener joined in 2013. What was "the cause," exactly? Money is an obvious part of the answer; the company made money, and helped its clients make money. The product, though, was essentially surveillance--making "the cause" a little more complicated. This kind of progress and success for their own sake, and the tensions that arise from the ethically ambiguous growth in tech, form the core of Wiener's unforgettable debut memoir, Uncanny Valley, a portrait of her arrival, immersion and ultimate disillusionment in Silicon Valley.  

Uncanny Valley begins with Wiener treading water in a mostly thankless job in New York City as an assistant in book publishing. Though the position affords her proximity to literature and art, Wiener founders as she seeks meaning in an environment that feels like it actually holds very little of it. The work is financially unsustainable, and Wiener craves change. Her transition to the tech industry is fairly natural: she joins a startup, three men developing an e-reader app. Her role was at times secretarial, at times creative and at times rewarding. At other times, it was clear the fit wasn't right. Still, the experience led her to seek further opportunities across the country, in tech mecca.

"When I arrived... in San Francisco, with a fresh haircut and two fraying duffel bags, I felt intrepid and pioneering," writes Wiener. "I did not know that thousands of people had already headed west for a crack at the new American dream, that they had been doing so for years. I was, by many standards, late." Late is relative, of course. Wiener arrives in time to work at numerous startups that have since become enormously successful, and in time to still see firsthand the effects of the tech boom on the Bay Area writ large.

Her first position is in customer support. As she gains proficiency--and maybe more importantly, confidence--she thrives. But as she embeds more deeply into the startup scene and its tech-fetishizing culture, an unsettling feeling grows as well. Unfettered, underregulated progress and belief systems that prioritize development and momentum above all else led to credos like "Move fast and break things" and, of course, the classic "Ask forgiveness, not permission."

Wiener recounts glamorous parties, boring meetings, gross wealth, imposter syndrome. The camaraderie of the tech workers is warm at times, a bath of pleasure-seeking alongside progress-seeking. But the pace is breakneck. Breakneck, as well, are her efforts to find a place to belong in San Francisco as the city changes. Wiener worries about the repercussions of the tsunami of development, both on the people of the city and the culture at large: "The city, trapped in nostalgia for its own mythology, stuck in a hallucination of a halcyon past, had not quite caught up to the newfound momentum of tech's dark triad: capital, power, and a bland, overcorrected, heterosexual masculinity."

These issues are uncomfortable truths in Uncanny Valley. "Sexism, misogyny, and objectification did not define the workplace--but they were everywhere. Like wallpaper, like air," writes Wiener. Issues involving trust, surveillance and Big Data add further complication. Yet Wiener mines sharp humor from all of these tensions.

"Like a woman who is constantly PMSing, a twenty-three-year-old founder of a crowd funding platform wrote about the climate," she recalls. "The extension of casual misogyny to weather was creative, but the digital ambassadors didn't seem to like actual women, either: they whined that the women in San Francisco were fives, not tens, and whined that there weren't enough of them."

But though she can joke about it, Wiener could not--and has not--stayed quiet about it: "I was the feminist killjoy. I did not pick my battles. I died on every available hill." As she fought for a better workplace, and a better culture, she also shifted industries again--to her growing writing career and increasing political advocacy. Throughout, she acknowledges the privileges she holds and the struggles of those who lack the same opportunities and access.

So Uncanny Valley is a story about work, but it's also a story of capitalism and complicity. It's a story of progress, greed, principles, EDM and a lot of kombucha. It's alternately outrageous and outraging. What makes Uncanny Valley unforgettable is not just Wiener's unique take on tech, but the fun of being along on the journey with her. Her immense intelligence and facility with language make the pages fly. She's generous, quippy, introspective and always self-deprecating. Technophobes have nothing to fear; she employs jargon mainly for laughs.

Despite these strengths, it is clear Wiener was undervalued--financially, certainly--in the tech industry. Wiener still almost seems skeptical that her skills hold value. They do, of course, but her meditations on how monetary, cultural and intrinsic value rarely overlap help explicate what "value" is, and how often that may be conflated with "power." The CEO of a company Wiener worked for once wrote about her, not realizing she would see it, "She's too interested in learning, not doing." Yet the cost of what happens when progress is made for progress's sake is one Wiener asks readers, urgently, to consider. Perhaps getting away from the kind of thinking that separates learning from doing is a first step. --Katie Weed

Anna Wiener writes about Silicon Valley and tech culture for the New Yorker. Her debut, Uncanny Valley: A Memoir (MCD/Farrar, Straus and Giroux, January 2020), explores her experiences moving from the publishing industry to the tech industry, and reflects on the near-surreal pace--and consequences--of rapid innovation and the fetishization of "progress." Wiener lives in San Francisco.

This is an extremely funny book. Yet, the humor invites readers to consider that what goes on in the tech industry often isn't funny at all. How did you approach that? 

Thank you! I'm so glad you thought the book was funny, and not purely horrifying. There's so much about Silicon Valley that is fundamentally humorous, and it has to be humorous because otherwise it's too grim. The way people speak to each other; corporate feudalism; the hubris; the pervasive, frantic branding. I willingly participated in an adult scavenger hunt with my coworkers. That's bleak. (Should people be paid overtime for after-hours team-building exercises? Probably.) So I can't really take credit. In most cases, I was just documenting. 

Rebecca Solnit--author of Men Explain Things to Me--deemed you "Joan Didion at a start up." 

How incredibly generous of her, no? I'm a longtime admirer of Rebecca Solnit's writing, including her essays about San Francisco during the current tech boom, and a longtime admirer of Didion's, so the comparison means a lot to me, though I don't think it's deserved. It also makes me wonder if Joan Didion has ever been in a startup office. Imagine Joan Didion in a WeWork. Joan Didion within 10 yards of a RipStik. She would never. The thought makes me want to die.

Readers will notice early on your decision not to "name names," though we can likely deduce which company's app you used to rent a room in someone's home, or which pink-mustachioed rideshare you used to commute. What led to that decision?

I wanted to avoid naming companies, services and executives to shy away from cultural associations, and to do my best to keep the book from feeling dated. I also like generics. They're playful and ambiguous. In many ways, the actual companies I worked for don't really matter: on the cultural level, they could have been any number of startups from this period, just as a lot of the executives--specifically with respect to behavior--could have been any number of Silicon Valley executives. My hope is that stripping companies down to their functions will raise questions about the extent to which we actually need these services. (The way I thought about it was basically, How might I explain this to someone in 40 years? There is no way to explain Groupon to someone in the future without sounding completely frivolous, ridiculous.)

You do, however, name numbers--even sharing how much you made exercising your stock options.

Concrete numbers are helpful, I think (I hope!) in animating incentives and stakes. There's also a lot of information out there about what programmers make--the median salary at Facebook is $240,000, etc., etc.--but there's less information about salaries for nontechnical, entry-level employees, and I suspect there's more variation, especially at startups. In general, I think there should be more transparency around compensation, especially in industries like tech where the pay gap can be dramatic. There also needs to be more talk about equity. For people who work at private, venture-backed companies, whether or not you have equity can be the difference between maintaining a nice 401K and building generational wealth. A lot of people don't know the right questions to ask, especially starting out, and companies will take advantage of that.

One very relatable thing you write about is struggling with the urge to please those around you. How did you navigate that as you relayed stories that might not please those who recognize themselves in the book? 

A question right at the beating heart of the Venn diagram of "writing memoir" and "being a woman!" Both, for me, are ongoing crises. In this case, I'm not particularly interested in pleasing people simply on the basis of their structural position. The unnamed founders, executives and venture capitalists in the book are people with power and influence. If I were to withhold criticism, whom would that protect, and what systems would it reinforce? (The people who are named in the book--friends, coworkers--did have a chance to read their sections, and we worked together to make changes to anything they felt wasn't quite right.)

Uncanny Valley offers something like a time capsule of the San Francisco Bay Area, not just in tech but in terms of the humanitarian crises the industry engenders. How has the city changed in your time there? How has what you notice about it changed?

When I moved here, in early 2013, I knew I had missed something, but I thought the change was over. I didn't realize I was actually catching the beginning of a transition. We're still in it. I don't know how, or when, this ends. The biggest issue right now is probably housing. It has become very, very expensive to live in San Francisco, and this wasn't a cheap city to begin with. The homeless population has risen by 30% in the past two years. A lot of people are struggling. At the same time, there's all this money sloshing around. All these new, ridiculous restaurants. Empty storefronts. Airbnbs. A surplus of Lyft and Uber drivers, some of whom travel from Sacramento or Los Angeles, many of whom spend a good part of the day idling. All these Victorian houses being flipped, after--the indignity--getting painted gray.

It's no longer a destination for artists or musicians or writers, and you can see the culture shifting. It's complicated: there are a lot of factors contributing to the housing crisis (and attendant issues), and tech is just one of them--but tech is an accelerant of sorts. San Francisco is a small city. The tech industry is oriented toward growth and speed. As a result, it's like a swift, blunt force. 

At one company, in the face of rampant sexism, you stopped writing publicly under your own name. Did you consider writing this book Jane Austen-style, or whistleblower style, anonymously? "By a Lady in Tech," say?

I didn't. I did consider writing it as fiction, but I didn't want the book to be mistaken for satire.

What's next for you? Have you picked up the bass yet?

Bass remains the white whale; what is wrong with me?? I've been enjoying writing dispatches from Silicon Valley for the New Yorker website--I'm excited to do more of those. I'd like to write fiction again, just to switch gears for a minute and see if I can do it. I'll probably have at least a few nights of regretting that I don't know JavaScript. I still worry, every day, about marketable skills. --Katie Weed