Episode 26: Uncanny Valley

Anna Wiener speaks with editor Dayna Tortorici about her essay “Uncanny Valley,” a fictionalized account of her time working in the Silicon Valley tech industry. Anna and Dayna discuss the background of the story and how it became one of the magazine’s most popular pieces.

Hosted by Aaron Braun, Malcolm Donaldson, Emily Lyver, and Eric Wen
Audio Engineer: Malcolm Donaldson
Produced by Aaron Braun, Malcolm Donaldson, Emily Lyver, and Eric Wen
Graphics by Eric Wen
Music from Dinosaur L, The Smiths, The Clean, Neil Young, Gary Numan, Teengirl Fantasy

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Episode Transcript


Malcolm Donaldson: Hi, and welcome to the n+1 podcast. In Issue 25, Slow Burn, Anna Wiener contributed her story, “Uncanny Valley,” a fictionalized account of her time working in the San Francisco tech world. Anna talks with Dayna Tortorici, who edited the piece, about how this quickly became one of the magazine’s most popular pieces, and why.

SEGMENT: Interview with Anna Wiener

Dayna Tortorici: I want to start by telling people about how this article came to be. What’s your story?

Anna Wiener: The story that I have been telling people is that I started writing this as a way to entertain you.

DT: To entertain me?

AW: To entertain you.

DT: Me personally?

AW: Yeah, you specifically. After you came to San Francisco and stayed with me and sort of saw a little bit of the tech industry and the start-up world . . . I was under the impression, perhaps the delusion, that I was writing these anecdotes for you. But I think you have a different story.

DT: I do, I have a little bit of a different story. I do remember coming to stay with you in San Francisco, and I remember going to the coffee shop around the corner and being totally delighted and surprised by the fact that everyone who was working on their laptops seemed to be editing code in public, which I had never seen before. Because in other cities, when people are sitting in coffee shops working on their laptops, they’re . . . I don’t know, writing their novels or their screenplays, or looking at Twitter. And so I came back and told you how amazing it is when things conform to type, because it was all so perfectly clichéd. And then I asked you if you had written about this, and you said you had some stuff stowed away. And then I forgot. And months later, I asked you to review a book about women and feminism and sexism in tech. And to my memory, you said, “Hey, I read the book, it’s fine, but I don’t really have much to say about it. Can I write something else instead?” And then you sent me the first draft of the piece.

AW Right. That’s right.

DT: Is that correct?

AW: That is correct. I guess I’ve deliberately washed that out of my mind. Lean Out is a book of first-person essays by women in tech about working in tech, and it’s very critical. It’s good, but I think I might’ve written to you that it felt like a zine to me.

DT: You did.

AW: So it didn’t seem like I needed to add anything to that conversation. But I do wonder if writing this piece in the first person dovetails with that project more than I might have acknowledged initially.

DT: So then what happened? You sent me the piece. I sent it to Nikil Saval, our coeditor. He was delighted by it because he used to live in San Francisco, and of course when he was writing his book, Cubed, about the history of the office, he visited many tech offices. And he said that the piece was very true to what he had seen. And I think we just . . . ran with it.

AW: Sort of. I then rewrote the piece in a fit of anxiety. I wanted to be compassionate to everyone involved. These are people I’m friends with, these are the people that I date—they’re the people I admire and respect. So anything critical felt a little bit like a betrayal. Even though there aren’t that many specific characters in the piece and a lot of them are composites. It’s fiction. So I rewrote it in a much softer tone—it was a little mopier and had longer sections about my failed love life, which was totally off topic. There was some silence after I sent in this second draft, this updated version, which was more about a girl alone in the city than a specific piece about start-up life. My start-up life. And then you sent back a version. You were like, “so I brought this to the editorial meeting, and I cobbled together pieces from both drafts,” and I was like . . . that’s a nightmare. But it turned out a lot better than what I had written. I was really hedging, in your words—trying not to offend anyone, trying not to poke fun without qualifying at length. And so I think you had more of a vision for what this piece was than I did. And for what the value of this kind of writing would be. The value of this kind of writing is not to criticize and apologize. I think you really teased out a voice from the piece.

DT: Well, not to be like, “no, you!” but it was all there in the beginning. What surprised me from the jump was that anyone who wanted to write about start-up culture for n+1 would probably be much meaner, would be more likely to paint in broader strokes and just anti-Silicon Valley in the style of, say, Rebecca Solnit. The things you were hedging on were so anodyne. You wrote that all of this was “getting some kids unfathomably rich,” but then you were like, “well, technically they’re not kids, and technically it’s the shareholders who get rich.” And I was like, “Come on. That’s a really good line.”

AW: You were like, “that’s exactly what someone drunk and indignant would say.”

DT: Yes.

AW: Which is true.

DT: That’s what I would say.

AW: I probably wrote it while drunk, indignantly, so . . .

DT: Which is the best way to write.

AW: I don’t write drunk. I just write stoned and then email it to myself.

DT: Yeah, what’s your . . . This is now a Paris Review interview.

AW: What’s my process?

DT: What’s your process?

AW: Well, Dayna, I portion out six almonds into a small dish for breakfast.

DT: Then I take some sour diesel reserve and sprinkle it onto my almonds.

AW: And then I meditate for eight hours.

DT: I wanted to talk about the response to the piece, because it seemed to catch you by surprise.

AW: That’s for sure. I’ve said this before, and I apologize in advance, but I really didn’t think anyone was going to read it. You know, n+1 has a really dedicated niche audience on the east coast—that would be my guess. The fact that anyone was reading it in the first place was surprising to me because I figured that people on the east coast wouldn’t care that much about a narrative about the tech industry in San Francisco, and I didn’t think anyone in the tech industry would ever see it. Which was naive because it was on the internet.

DT: People who work on the internet love reading about the internet on the internet.

AW: I think that’s true. And also, I think the tech industry is typically represented in one of two ways. The more common one is this snarky, shady, quasi-satirical way that doesn’t really acknowledge that the industry is full of people who, for better or for worse, really believe in what they’re doing. To make fun of it in that way isn’t nuanced. And the other way is through a non-critical tech press, which is boostery—and has to be, because they need access. So for people to read something about the industry that was neither boostery nor mean was interesting, I think. I don’t mean to say that I wrote anything about the tech industry that was definitive. I think there’s a lot of space for people to contribute between those two poles.

DT: Can I tell you my theory about why people liked it so much?

AW: Yes.

DT: This is a completely unsubstantiated theory.

AW: That’s the best kind of theory.

DT: I think that one of the reasons it hit home for so many people (it’s one of the most widely circulated pieces n+1 has published online, second only, I think, to the Pussy Riot closing statements from 2012) was that you wrote about a group of people who spend a lot of time looking at a screen and thinking very carefully about how they present themselves on the screen and interact with other people on the screen and the entire universe that’s happening inside the screen. So the idea that they are visible to people beyond the realm of the screen catches them off guard. It’s a very simple and sort of naive thing, but just to remember that you’re embodied and that other people can see you in the office with your shot blocks and your baggies of wet meat and the things you say in person “off the record” . . . I think a lot of people didn’t feel seen, in that way. They feel very seen in the register they’re used to presenting themselves in, but not as humans in the workplace.

AW: That’s interesting. The embodied workplace can go one of two ways. In a lot of small companies there’s a bit of what we used to call the ass-in-chair metric, where the number of hours you were sitting at your desk was noted. Your physical presence in the office was very important. I’ve spoken to a lot of people—especially a lot of women who have children—who say that it’s hard to work at a small start-up. This is probably true for a lot of different companies, but it’s hard to work at small start-ups because leaving at 5 PM to pick up your kids from after-school programs puts you in a place of scrutiny where people think you’re not doing your job, or you’re not doing your job as well as the people who are in the office until 9 PM. In some ways, you really do need to be seen in these workplaces. But on the flip side of that, I work in a company where more than half of the 550-plus employees don’t report in to the San Francisco office—they don’t work in any office. I work for someone who lives in Amsterdam, and the people on my team are from all over the United States, and I’m in New York right now, and I worked this morning from six until noon. (I don’t think anyone else on my team noticed that that was a shift, really.) So I don’t really agree that it’s people who felt seen for the first time, physically, but I’m really compelled by that thesis.

DT: Unsubstantiated theory.

AW: Unsubstantiated theory.

DT: I’d like to read you a tweet.

AW: I wish you would.

DT: By Chris Sacca, who is on ABC’s Shark Tank. He says, “If you’ve worked in Silicon Valley, you’ll recognize yourself in this genius @annawiener piece. Frankly it should start with a trigger warning.” So this is one of many guys who tweeted the piece. Jonah Peretti of BuzzFeed tweeted the piece. This guy at the White House said something about how he was scared to read the piece for a week, but then he was finally going to read it.

AW: That might be the great achievement of my writing career: scaring a man on the internet away from reading it.

DT: What were some notable reactions to your piece?

AW: I got a lot of email.

DT: From whom?

AW: Mostly from people who worked in tech or once worked in tech. Some people who have worked in tech for twenty years who wrote to say that it looks like not much has changed.

DT: People who are still in tech or people who have left?

AW: Both. I got a lot of emails from people who work in the industry now and who saw something articulated that they recognized from their own experience—or just felt was missing from the larger narratives we tend to hear about the tech industry. I do want to clarify that I mean the start-up universe. There’s a difference, culturally, between working at Google and working at a twenty-person company. Having never worked at Google I can’t speak to what the former experience is like. But when you work at a start-up—especially when it’s quite small—not only do you know every other employee, but you basically know what’s going on in most parts of the business. And your investment is not necessarily more personal, but perhaps it’s more distributed across a company.

DT: What do you mean?

AW: What I’m trying to say is that this is very much a start-up story and not a tech industry story.

DT: Got it.

AW: So I tended to hear from people who had worked at early-stage start-ups, or still do.

DT: You texted me to say that you were getting a lot of emails from men.

AW: I continue to get a lot of emails from men.

DT: Are these men asking you out?

AW: I don’t think so. Maybe. I’ve been trying to figure this out.

DT: But they’re not not asking you out.

AW: Well, no. I don’t think anyone’s explicitly asking me out. I think people maybe identified a kindred spirit in this narrative voice. A couple people asked me for coffee or for a beer—there was one email that I thought was particularly funny, when a guy said “it would be fun to meet you.” I laughed and laughed because no one I’ve ever met has ever called me fun, and I’m just so tickled by that assumption. But mostly, I think people were just looking to connect. And a big part of that is that you really do connect with coworkers, and you feel as if you’re in this thing together. You get to know each other’s partners, you get to spend from 9 AM to 11 PM in the same space getting meals together, getting drunk together. It can be really hard to sort of step outside of that and say, “wait a minute, I actually do feel like an outsider in this culture we’ve created.” Maybe for some people, I’m the outsider that they want to talk to, like we’re at a party and they’ve identified me as the person standing against the wall looking uncomfortable.

DT: So there aren’t that many public wallflowers. All the public expressions of identity are either “we’re all in!” or “I’m quitting because this is not for me.” People seem to be surprised that you still work in tech.

AW: I understand that surprise.

DT: They assume that you had worked at this job and then quit.

AW: Which I did. I just quit with another job in hand, also in the tech industry.

DT: Speaking of criticism, there are two moments in the piece where you quite gently call out some either unconsciously or consciously sexist behavior, or mostly just unprofessional behavior. One is an anecdote about being interviewed by the technical cofounder of a company who says he’s never interviewed anyone before, so he just has you take the LSAT. You do well, but then you say you feel lower than low for having taken it. And the other one is a guy whose screensaver—or maybe the background of his phone—is an animated gif of breasts bouncing.

AW: That’s an app on his smart watch.

DT: A skin, as it were. Did those people reach out to you in any way? Did they recognize themselves in those anecdotes?

AW: Some of them did. My former coworker and friend with the smart watch app emailed me and apologized profusely. He said he didn’t even realize when he was in it that this could have been alienating.

DT: I saw a tweet about the piece that said something like, “this is the most deliberately not shared but privately emailed by women piece I’ve ever read in my life.” Which is a weird construction, but I took it to mean that there are so many women in my life who are reading this piece, emailing it to their friends, sharing it on private Slack channels, but not posting it on social media. Because it speaks some truth about the pervasive—if sometimes anodyne—sexism of Silicon Valley. I was curious about what you thought of that—and also if you had any theories about why people didn’t feel comfortable sharing it publicly. Because it’s not a terribly subversive piece—it was shared very widely by men and embraced wholeheartedly by men.

AW: There are a lot of questions in that question.

DT: I know. I’m sorry.

AW: As an editor, or as a reader, did you think that it was a piece about sexism?

DT: Not primarily. I wouldn’t say that it’s a piece about sexism, but I did think of it as a piece that addressed sexism in start-up culture, or the sexism that is inevitable—unfortunately—in male-dominated workplaces. One of my very best friends worked in tech, but she quit because she was so tired of having to fight for very basic dignities at work, like being granted the same benefits and titles as her male co-engineers. So hearing about the culture from her, I was sensitive to it in what you were writing. The section where you talk about writing the email to your mom, and how she tells you not to put complaints about sexism in writing unless you have a lawyer at the ready—that section drove it home. There’s also been some really good writing about this recently in the context of the literary world. I’m thinking specifically of Jia Tolentino’s Jezebel piece about VIDA. There’s a desire for accountability greater than nothing, but less than something that would be penalized by law. You see the legal system—including NDAs—used by men all the time to quash “false accusations” of sexual harassment before they even happen. So here you were, calmly noting to your own mother the things you’re seeing at work and expecting her to tell you that you’re the change this industry needs, and instead she told you—very wisely—not to put complaints about sexism in writing unless you have a lawyer at the ready. This speaks volumes to me about a culture that’s armed with many legal instruments to prevent certain kinds of conversations from even happening. Which is to say that I did think it was a piece about sexism, but not primarily so—I didn’t think that was its only or central merit, or its central aim.

DT: I want to talk about your NDA. I know you can’t talk about your NDA.

AW: We can talk about the NDA. NDAs are super common. Like, you sign an NDA when you walk into any tech company.

DT: You sign an NDA when you walk into most companies, I think.

AW: I signed an NDA when I walked into this apartment.

DT: I thought it was interesting how the NDA became a kind of formal constraint on the piece. For as long as people have written in the nonfiction genre—for as long as they’ve written longform literary journalism or memoir—writers have had to take on a certain responsibility to make sure that they’re comfortable with how they represent other people. They’ve had to be willing to accept the consequences of that representation. If there hadn’t been an NDA, you would have felt some sort of fidelity or responsibility to your friends and coworkers—you wouldn’t have wanted to put them on blast because you like them and you’re a nice person. But the NDA creates an obstacle that’s different from the dictates of journalism and different from the ethics of the journalist or the memoirist. It’s a legal hurdle that also affects this kind of writing. So I have two questions. First, did it feel like an impediment when you were writing, something that you were conscious of and had to edit around? Second, do you think that NDAs hamper—or in some ways prevent—more people from writing narratives like this?

AW: Those are good questions. It was an impediment, but maybe not in the way you’re suggesting. An NDA isn’t there to protect people’s feelings. What I mainly wished I could have written about—but which I can’t and won’t write about—is what it’s like to work at a company where the product is a data analytics product. So a lot of your customers are other tech companies. Theoretically one might say that a lot of the customers of a company like that are other tech products. So when you’re working one-on-one with these different companies—many of which are well known software companies—you get some insights into how some of these businesses are doing. Even something as seemingly benign as going on-site to another company’s office—I wish I could write about that, because it’s so fun to see how these other companies are run, and what’s important to them, and who these people are who are building and selling and working on the apps that people use everyday. But that’s something I just really can’t get into for many reasons. That’s really where I felt impeded—it wasn’t emotional, it was just not getting to write about the ins and outs a little bit more. I’ve forgotten your second question.

DT: The second question was whether you think NDAs prevent people from writing more stuff like this.

AW: Well, there’s a difference between an NDA and a non-disparagement agreement, or a non-disparagement clause. The paperwork I signed when I joined this company included a non-disparagement clause, I believe. Or basically it said that within a year of leaving this company you agree not to—

DT: Talk shit.

AW: Yeah, you agree not to talk shit or do anything that would hamper the business.

DT: But it only lasts a year?

AW: It lasts a year.

DT: They’re really counting on people to not hold grudges. They’re like, “the average grudge lasts one calendar year.”

AW: Data analytics for grudges.

DT: I could use that in my life.

AW: I do know people who quit or got fired, and in order to get a severance package, they had to sign a non-disparagement agreement that is longer than a year. I think this is also boilerplate. You also agree not to poach people for your own company, or where you go next, or you agree not to work with a competitor. I think the assumption is that after a year, your sense of trade secrets is slightly diminished. I know no trade secrets, so this doesn’t apply to me. I’ve read a lot of first-person accounts of working at start-ups. People post them on their blogs, they post them on Medium, they post them on Twitter and write tweetstorms that are really specific and negative and very personal. And that has to do with the fact that in some cases, companies don’t ask their early employees to sign an NDA because it doesn’t occur to them—and also because some people are just ballsier than I am, so to speak. People have more guts than I do. What was the name of that book that came out recently? Disrupted.

DT: I had never heard about that book, and then I saw people refer to it in reference to your piece. They kept saying that your piece was better than that book.

AW: I resent the comparison, although I understand why people would compare the two. Dan Lyons is a journalist, a former editor of Valleywag. He went to work for a company in Boston, a big company I’m forgetting the name of, and he worked there for a year and then wrote a tell-all book about it, which is exactly the sort of writing I hope never to do. I don’t have beef. He’s a good writer, and he’s very funny. But my sense is that he took this job so that he could write this book.

DT: So it seems opportunistic. And disingenuous.

AW: It does. I would be lucky to have the sense of humor he has, but Disrupted really skewers a culture without investigating its human side. And I guess I’m just sort of sensitive about it because I did join this industry and did feel a part of it for a while—I always felt like an outsider, but I did want to be a part of it and joined it out of sincere curiosity and excitement, as I think so many people do.

DT: Do you think it’s a bubble?

AW: The economy?

DT: The industry specifically. There’s a saying that as soon as the schoolteachers and preachers get in on the action, you know you have a bubble. It seems like everybody and their mom has an idea for an app. Does this mean that this is the beginning of the end?

AW: No, I think that’s the point of the technology—to be accessible for everyone and their mom and their priest to have an app idea. That’s the point. Culturally, sure there’s a bubble. But I don’t think it’s any more of a bubble than the one I lived in when I worked in publishing. All my friends worked in publishing, and all my conversations were about books. And I loved that bubble. And I think the only reason this bubble is getting so much publicity is because unlike publishing, there’s a lot of money and power associated with it.

AW: Ellen Ullman told me a story when I was interviewing her for a profile last year . . . this isn’t really my story to share, but I’m going to share it anyway because it might be interesting. She told me about how she went to speak to a college class about how the industry really needs to change—about how more queer people, more people of color, and more women should be encouraged to move into the industry, and that that’s how tech is going to move forward—that’s how it’s going to change. She said that a guy came up to her afterward—a shy-looking young man, a little socially awkward. And he said, “it’s not gonna change that much, though, is it?” It hadn’t occurred to her that for him, and for people like him, everything that makes the industry so hard to break into—so alienating for people who are not the archetype of the soft-spoken nerdy coder—actually made it safe.

DT: I confess I’m much less sympathetic than you are. The first thing I think is . . . well, that’s great, but did they have to destroy the city of San Francisco to build their safe space? And did they need to become the richest people in the world in the process? And isn’t it kind of scary that people who feel like outcasts or nerds precisely because they lack social skills are now tasked with social responsibility because they are the wealthiest people in the country? Yikes!

AW: Yes, all of this is great. I’m on board with all of this.

DT: Well, thanks, Anna.

AW: Thank you, Dayna. Longtime listener, first-time caller. Such a pleasure.


Malcolm Donaldson: Thank you to Anna Wiener and Dayna Tortorici. The n+1 podcast is produced by Malcolm Donaldson, Eric Wen, Aaron Braun, and Emily Lyver. Thanks for listening.

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