Meet Anna Wiener, the debut author whose memoir could change Silicon Valley

What’s a debut author to do after being called, by Rebecca Solnit of all people, “Joan Didion at a start-up”? After receiving glowing reviews and splashy profiles in high-profile publications like the New York Times? If you’re Anna Wiener, author of the highly praised book in question and potential second coming of Didion, you go on a book tour and let, in the most millennial of ways, your uncertainties run amok.

“A lot of the attention on me is just confusing,” Wiener tells EW from her Boston tour stop for Uncanny Valley: A Memoir. “I’m a pretty shy, private person. I’m not much of a brand-builder, so that’s been shocking.”

Uncanny Valley tells the story of a fairly normal person trying to make sense of the completely abnormal social structures in the world of San Francisco start-ups. Wiener was in her early twenties, living in Brooklyn and barely getting by (both financially and spiritually) as a book publishing assistant, when she pressed pause on her East Coast literary life and headed west for the promise of, well, anything solid.

She started working in customer service in the rapidly growing start-up scene and quickly took notice of Silicon Valley’s oddities — many of which would later wind up in her memoir. Uncanny Valley grew out of a piece Wiener wrote for the literary magazine n+1, meant to be a book review for Lean Out (itself a retort to the Sheryl Sandberg tome Lean In). “Once I started writing [the review], I realized there was all this ambition and disappointment and failure and disillusionment that I was experiencing and witnessing,” Wiener says.

The memoir that came to be is a brutally honest investigation of the intentions behind Silicon Valley’s often megalomaniacal founders, the wild (to outsiders) cultures and practices of tech bros, and Wiener’s own evolving personal life. It results in incredibly prescient and humorous observations.

On her late entrance to the tech boom, she writes: “While my future peers were hiring wealth managers and going on meditation retreats to Bali to pursue 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.” On a co-worker at her first startup: “I could picture him making seitan stir-fry, suggesting a hike in the rain…. I had the uneasy feeling he could persuade me to do anything: bike across America, join a cult.” On San Francisco itself: “In the absence of vibrant cultural institutions, the pleasure center of the industry might have just been exercise: people courted the sublime on trail runs and day hikes…. They dressed for work as if embarking on an alpine expedition.”

It’s easy to see why the literary community had gravitated toward Wiener’s memoir so aggressively: She’s the latest in a spate of millennial women (Jia Tolentino, Sally Rooney) to articulate the motivations of their generation in a way that feels new, even to the people already thinking those thoughts. (Tolentino has also heaped praise on Weiner.) Uncanny Valley hit bookshelves Jan. 14 with high anticipation, a phenomenon Wiener describes as highly surreal and strange, especially after years of professional and personal uncertainty.

“In the writing process I had a lot of doubt and anxiety,” she says. “I felt really alienated and depressed for the 18 months I was putting together the manuscript. That process isn’t shown when all you see is this published book with the beautiful cover suddenly out in the world for people to engage with.”

Another contingent taking notice of Uncanny Valley is the very group it exposes. Wiener doesn’t name any companies or executives in the book — partly to acknowledge that the places she worked could stand in for any in the industry, and partly as a “rejection of the individualism that Silicon Valley tends to champion” — but it’s easy enough to deduce who and what she’s talking about. She openly discusses the disturbing elements of God Mode, in which tech employees can see everything about their users, and chronicles office behavior that ranges from offensive conversation that could have once been deemed “locker room talk” to blatant sexual harassment. She continually reminds the reader that Google is more of an advertising platform than a search engine.

During her five-plus years working in Silicon Valley, she never actually intended to write such a critique; she wasn’t some disgruntled employee scribbling missives for a future tell-all. Instead, like many people, she took stock after the 2016 election.

“At the end of 2017 if felt like something had come to a close,” she says of the tech industry. “I don’t mean anything had fallen apart, but that the stories from within Silicon Valley were exposed as being, if not fraudulent, then disingenuous. The party had ended, and I wanted to get everything down as quickly as possible before it disappeared from memory.”

For those wondering how she was able to simultaneously offer a detailed account of her jobs’ absurdities and wax poetic, Weiner had a habit of emailing herself notes (with lines like “Body optimization: look into that”) and went back through correspondence and performance reviews to jog her memory. “When I started writing the book I was feeling cynical and defeated, and it was important for me to be able to channel the enthusiasm I had at 25, 26 when I was just starting out,” she says of her journey down memory lane.

Uncanny Valley spans several years of ups and downs, though Wiener was limited by non-disparagement agreements and an altruistic desire to leave contempt out of the equation. “I wanted to err on the side of generosity and give people the benefit of the doubt,” she says. “It is a critique, but I didn’t want anything to be in the book for the sake of making someone a punchline or expressing some pent-up aggravation.”

Regarding the balance she ultimately strikes, it’s still easy to feel despair by her conclusion, especially if you want to believe that we can avoid succumbing to the power of tech behemoths. But this isn’t a novel, it’s a memoir, which means our protagonist is a real person. You can Google the author for a more soothing ending; turns out, she got a huge book deal.

As for Silicon Valley? That leaves some dread, and a cursory Google search will only make it worse. Anna Wiener has some words for that, too.

“One of the biggest problems right now is that this is all treated like it’s inevitable,” she says. “[Tech companies] discuss their own platforms as though it’s inevitable we should have social networks on a global scale or fleets of contract workers who are exploited. I don’t think the industry can be trusted to correct itself, but I have to be optimistic. Otherwise what’s the point?”

Related content:
—Jim Butcher offers a sneak peek of upcoming novel Peace Talks
—See where Cassandra Clare is headed for her Chain of Gold tour
—These gorgeous new novels explore sex with empathy, complexity, and radical honesty