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Uncanny Valley: A Memoir by Anna Wiener – the highs and lows of real life in Silicon Valley



Every now and again a book comes along that sends a rumble through the tech industry and everything it stands for. Recent publications include 2018’s Bad Blood all about Elizabeth Holmes and the Theranos scandal, to last year’s Superpumped, which chronicled the growth-at-any-cost-mentality of Travis Kalanick’s Uber. 

An early contender for this year’s tech literary sensation is Uncanny Valley by Anna Wiener, a memoir of her time as a 25-year-old in Silicon Valley’s start-up world. Released last week in the UK, it’s already earned a place on the New York Times’ bestseller list and spawned think pieces and reviews for its outsider account of life inside the tech bubble, from the optimism of the early 2010s to the reckoning that has started to snowball since the 2016 US presidential election.

A New Yorker by birth, Wiener graduated into the peak of the 2009 recession before settling into a job as an assistant in publishing. Whilst reading about an e-reading app promising to disrupt the book industry she decides to apply for a role, which brought her into the tech world and, eventually, saw her working for Github, the open-source code platform which was later acquired by Microsoft for $7.5 billion.


Though she had worked in publishing, a career as a writer wasn’t part of her initial game plan. “I always enjoyed writing but felt maybe my utility was helping other people who were better writers put their books out in the world rather than focus on my own writing as a career path,” she explains when we chat on the phone from a hotel in Washington D.C as part of her book tour. Despite moving into tech, she still kept a foot in the literary world by doing occasional book reviews for a Brooklyn-based magazine, n+1 which was where the initial idea for Uncanny Valley came about. 

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“I was supposed to write a review of a book called Lean Out, a collection of essays in response to [Facebook COO] Sheryl Sandberg’s Lean In, and that review morphed into a series of anecdotes and observations of my own life in Silicon Valley. It wasn’t supposed to be a personal piece, it emerged that that was more exciting to me and my editor.” 

Uncanny Valley details the highs and lows of life in tech — from the high salaries, understanding code and feeling part of a cohesive movement, to the casual sexism, rising homelessness in San Francisco, and the problems of the far-right which exploded across tech platforms during the election. 

The sexism aspects are particularly startling. There’s the co-worker that asks her to slap him across the face whenever they were out drinking. The time the start-up hired its first female engineer and an account manager remarks, “I feel sorry. Everyone’s going to hit on her.” She asks colleagues not to use the word “bitch” in work chat rooms and ponders speaking out about loud conversations offering graphic details about threesomes in the open-plan office. 

Then there’s the time on a work ski trip, when a colleague repeatedly tries to put his hands down her pants in a ride home. “I kept the conversation going, pushing his hands away, sliding toward the window,” she writes. 

Uncanny Valley: A Memoir of life in Silicon Valley is out now

Recalling her feelings and responses to her day-to-day life in tech wasn’t too difficult for Wiener. Whilst she didn’t keep a diary, she used emails she sent to her friends back in New York to help her navigate to the headspace she was in at the time. “They were like old fashioned correspondence of us figuring out the version of the same [questions] – what does it look like to find meaning in work, is that where we should find meaning, are we ambitious, are we unambitious, what do we want?”

It feels natural that these were the questions Wiener was grappling with at the time. The almost detached nature of her writing as she recalls key moments in her life sometimes feels similar to Sally Rooney’s hit Conversations With Friends. Though a novel, it keenly explores the millennial feeling of something happening that the writer is unsure of how to respond to and offers it up to the reader for their own uncertain judgement. 

“When you’re in something that’s all-consuming it’s hard to understand there’s an exit door,” she explains. “Reading those emails, it’s like ‘oh my god I should have just gotten another job’, I should have known it was all shenanigans. But I think in my 20s I didn’t have a ton of experience with work or anything else so it seemed normal. It seemed that if things were going badly it was my fault because everyone else was going along with it.” 

This detached nature also appears in the way she describes the tech companies that dominate the valley and beyond. Airbnb is a “millennial-friendly platform for renting strangers’ bedrooms”, Facebook is the “social network everyone hated”, Amazon is “the online superstore”. Wiener says this was a stylistic decision. “I felt it was useful to describe what these companies did and their function in society. It highlights some of the absurdity of the fact they are basically monopolies and that they have so much power and influence.” 

When it came to the companies and start-ups she worked for, the lack of naming also pointed to how similar they are. “A lot of them are interchangeable when it comes to the experience women and non-technical employees have. Companies where there’s the emphasis on speed, rapid growth, acceleration, high returns or monopoly, this is a culture that’s not specific to any one company.”

This also links to her wider argument in the book that this relentless culture is part of a wider issue of the Valley. “It is an ecosystem. There’s a consistent style of corporate culture in Silicon Valley especially among start-ups and so to single any one company out didn’t make sense.” 

“I don’t believe in the utopian potential in the tech industry, I haven’t been given any evidence to believe that it’s different. There are aesthetic and cultural differences but at the end of the day these are corporations like any other and should be regulated.”

Her experience in tech has unsurprisingly affected how she approaches technology in her own life from not using Facebook to trying to spend less time on the internet. Though Wiener says she tries to not buy things on Amazon, she is critical of the emphasis screentime tools put on the user, not the creator. 

“The conversation around responsible and ethical consumption of tech puts so much responsibility on the individual. I think we should be talking more about how these products are designed for constant engagement.”

Despite her negative experiences in the industry, Wiener still lives in San Francisco and is now able to explore tech as a writer for publications such as the New Yorker, which she says will hope to satisfy her curiosity around it. Mainly, she hopes Uncanny Valley helps to reject some of the mythology the industry has cultivated.

“I think the book is ambivalent and my hope is that it can encourage ambivalence in one direction or another. I hope it demystifies the time and place for people and that is generative.” 

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