Q+A: Anna Weiner, Author of “Uncanny Valley”

Anna Wiener’s bleakly hilarious tech memoir probes the dazzling and ultimately hollow world of Silicon Valley.

Interview by Mae Rice

Anna Wiener’s tech memoir Uncanny Valley comes out this week after months of anticipation, during which an excerpt ran in the New Yorker and Universal optioned the film rights. Based on an n+1 essay of the same title, Wiener’s bleakly hilarious book tracks her career at a sequence of tech companies, first in New York and then in Silicon Valley. She works at an e-book app, then a B2B data startup “crushing it in the Valley” (her co-workers’ words), then an open-source startup. Wiener drinks the tech world Kool-Aid at first, but her perspective gradually shifts. Ultimately, she leaves her job to write, which is not a spoiler so much as a public fact.

Today, Wiener is a New Yorker contributor focusing on tech and its attendant culture. She can make even the daily grind of moderating a libertarian-leaning message board speak movingly to the human condition. In Uncanny Valley, she writes about a common experience — having an office job — with an uncommon level of honesty about how the work felt validating and important, inane and morally ambiguous. Study Hall spoke to Wiener about the process of turning her work experience into a memoir.

This interview has been edited for length and clarity.

STUDY HALL: I loved your book, and I’m really interested in how people can ever write about work. You mentioned jokingly in a tweet that it could make you “unemployable in the ascendant industry of my generation.” Did you genuinely worry about that?

ANNA WIENER: When I started writing this book in 2017, the concerns I had were mostly about relationships with the people at the companies where I’d worked: my coworkers, my former coworkers, the executives. When you work at a small tech company, you form pretty intense bonds. Some relationships are transactional, in the way any workplace relationship might be, but a lot of them are really meaningful. You get to know people intimately. I also knew that people had their own paperwork to be concerned about. In interviewing coworkers for this book, I wound up making hybrid characters so you can’t identify who said what.

The book’s funny, right? It’s not an exposé. It’s not an inside tale of one particular company. It’s more about the emotional experience of being in this particular industry at this time. That’s not a style of writing a lot of people in tech are used to reading about their world. Tech is an industry where companies really expect and demand a certain style of fealty. It’s transgressive to say anything negative, even to your coworkers. I think that was another one of my anxieties — being the person who sticks their head out from the inside and says, “This doesn’t feel right.”

SH: How has the tech industry responded to your writing so far?

AW: After the n+1 article, or essay — I don’t know exactly what to call it, it’s like an essay-slash-fictionalized essay; it’s all true, but I did some time compression — I just got a lot of emails from people. A lot of emails saying “This is how I feel too, I didn’t know other people felt this way.” I thought for a while that I was working at a pretty unusual company, and it turned out that a lot of people had experienced similar management styles and mismanagement styles — just this all-in, ride-or-die corporate culture.

SH: Have you gotten any blowback from the executives themselves? Have they contacted you?

AW: Some have contacted me. I wouldn’t describe it as blowback, no.

SH: What drew you to writing about work and the memoir format?

AW: I just really enjoyed writing that n+1 essay, and hadn’t realized the extent to which there was material that was really interesting to me in my job in tech. That piece actually started as a review of a book called Lean Out, which was a collection of essays that was sort of a response to Lean In. I had been talking to Dayna Tortorici at n+1 about reviewing that, and maybe incorporating some anecdotes from my own experience into the review to make it more personal. Then it morphed into just being these anecdotes.

I didn’t have any intention of writing about work, but it was like I had opened a door to something and found a new room in my house. That’s why it became a memoir — I didn’t go in taking notes. I didn’t see these jobs as anything other than my jobs and my career path. I’d always wanted to write, obviously, but what I wanted to write was more short stories, personal essays about feeling lonely, and book reviews. Pretty far from what my day-to-day work was. Although I was also writing content marketing copy and stuff like that, and for a while thought that was a path.

SH: Your n+1 essay came out in 2016, and you left your third tech job in 2018. In that intervening space, did your view of your jobs change? There’s this part in the book where you mentioned dissociating at work, which made me think that towards the end, maybe there was a bit of an undercover feeling.

AW: It’s funny. My jobs in the tech industry were really different. The first one in San Francisco, I was in the office every day; it was emotionally very intense for me. I was also very new to the city, so I spent my spare time writing very long emails to friends. I have a lot of diary entries about my life from that time. The next job, I felt super burned out by the time I got to it, and it was also a remote-friendly workplace. I went into the office regularly for about a year, and then I started working from home. It was lonely. All my teammates worked elsewhere. I had fewer interactions with people, and the material from that period basically came from when I did go into the office, which was not that often.

Once I sold the book — that was in late 2017 — I was already starting to drift away from my work at that tech company, in part because I felt very burned out on doing content moderation, on seeing all this garbage every day. My manager at the time knew I sold the book, and was very supportive, but I did feel that it wasn’t right for me to be writing about the company while I was there. I left in February of 2018. I hadn’t written any of that part of the book yet, about that company.

SH: What was your research process for the book?

AW: Searching and reading a lot of old emails. Feeling very embarrassed for my 25-year-old self who was frantically trying to be good in a work culture that was totally foreign. Looking through old text messages. I did keep notes — not on the companies exactly, but in the way writers keep notes of dialogue or observations. My extremely scattered and horrible way of doing this is not to actually keep a notebook, but if I see something on the subway or if someone says something that I think is sort of funny, I’ll email it to myself. So I have several thousand emails to myself that are quotes or little pieces of dialogue from work and San Francisco more generally. And I always know, looking back at them, what the context is and who said it. The way that people talk in tech especially is so interesting and funny to me that sometimes I would just write down a quote like, “We are at war.” I would sit with those emails and they served as a memory cue.

Then I read up about the industry at that time, because I was totally oblivious to what was going on outside my little bubble at that first job in San Francisco. That was mostly the process. I did interview coworkers I’d worked with closely, and I interviewed, for the last place I worked, coworkers I hadn’t worked with closely who had been at the organization longer and been in different departments. Like, the engineering department experienced a lot of tumult. I wanted to make sure I was getting it right from their perspective.

SH: Were NDAs something you thought about while you were writing?

AW: Absolutely. The manuscript has been read by lawyers. I left every job voluntarily, but a lot of the people that I spoke with — most of them women — left their respective companies on pretty bad terms, by which I mean they were pushed out in one way or another. Or they had experienced certain things that the company wanted to make sure they kept under a non-disparagement agreement. Without getting too specific, I don’t want to out anyone — and actually, it’s not all women, men too — but some people did sign non-disparagement agreements. It’s tricky because a lot of people really can’t leave that much money on the table. I tried to do a pretty delicate dance around protecting people, protecting myself. I know I haven’t broken any of my agreements [with my previous employers]. I’m pretty clear on what I have signed, and it’s not violated.

SH: That’s great you know what you’ve signed. When I visit tech offices, often I sign paperwork and have no record of what I signed.

AW: You should be able to email those office managers and get that paperwork. I had to do that for Uber — I had been to their office as a tech worker but then I went as a journalist, and you know, I’m the same person, same paperwork applies. Usually you can email the support team and they escalate it to the right person.

But yeah, it’s wild. As an employee, when I left my tech company, I didn’t know I could say no to signing stuff. Often when you’re leaving a company, it’s emotional, there’s a lot of stuff going on, and paperwork’s flying everywhere. I wish more people knew that they could take it more slowly, and maybe speak to a lawyer, have it vetted. Often people forget that they can negotiate the terms of their departures.

SH: Your book doesn’t involve a lot of proper nouns. Instead it has a lot of these recurring, slightly abstracted tags, like “the search engine giant.” Were legal considerations a part of that choice?

AW: That was a stylistic choice. I think the only proper nouns were “Ripstik” and “Michael Jackson.” But it’s not hard to find out where I worked, and that’s fine. To me, that’s not the point of the book. It’s more about the broader culture, and what I’ve come to understand is a pretty common set of experiences. Those experiences are shaped by a system of incentives and interests and ways of thinking about the world.

So it’s a stylistic decision, and it’s also sort of a political decision, if that’s not too pretentious to say. I have this friend Moira Weigel who’s a brilliant writer and critic, and she lived in San Francisco for about a year and a half. We would have these conversations where I was getting really stressed out about something in the industry, or some relationship I had with someone, or Mark Zuckerburg, and she had this refrain which was—say, with respect to Mark Zuckerberg— “If Mark Zuckerberg didn’t exist, the industry would invent him.”

So the companies don’t have names, and the executives mostly don’t have names, because this is a system that’s almost indifferent to individuals despite the industry’s very strong strain of individualism, a sort of libertarian individualism. There is a ton of founder worship, and the personalities are strong but they also tend to be consistent. They’re interchangeable in a lot of ways.

SH: For writers interested in writing about their day jobs, what are important factors to consider?

AW: It’s funny because I never really considered these jobs my day job when I was in them. I never went into them planning to write about the companies. Without naming any names, there was a book that came out a few years ago written by a guy who had worked at a tech company in Boston. I felt that it was pretty clear that he had taken this job to write the book. And I felt that you could tell from the writing that he didn’t care about it, and that made it inherently less interesting to me as a reader. I felt that there were no stakes for him. If you’re doing undercover journalism in a workplace, I would say be a journalist about it.

SH: What about considerations for people more in your position: people looking back on their professional life, and wanting to write about it?

AW: It’s probably an evaluation of a combination of factors. Evaluating your commitment to the people you worked with. The legal consideration is a big one, obviously. It’s also really important not to come from a place of contempt. If you have an axe to grind, the reader can tell. I hope my writing doesn’t sound like I have an axe to grind. I feel very ambivalent about the experiences I had. Some of them I feel really clear on, actually, on a moral level, but for the most part, I’m ambivalent.

I wrote an essay years ago about a receptionist job I’d had at a production music company. I was only there for a little while; it was one of my first jobs right out of college. I made the mistake of not telling anyone there that I was writing it, and I also made the mistake of naming the company. It was not a mistake for legal reasons, but I think it was ungenerous of me. Some people are reading Uncanny Valley as an indictment, and it is in some ways, but I really did try to err on the side of generosity and fairness. Which might make it more of an indictment.

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