The type of sexism Anna Wiener describes in her debut memoir, “Uncanny Valley,” seeps. It seeps and creeps, until you can no longer look away. Until it seems to float up from the book’s very pages, filling the air.
At 25, my age now, Wiener left her job at a New York City literary agency to join a tech start-up. At the time, Wiener writes, Silicon Valley’s start-up scene was “what cynics called a bubble, optimists called the future, and my future coworkers, high on the fumes of world-historical potential, breathlessly called the ecosystem.”
In the intervening years, Wiener would join a different start-up; move to San Francisco; join a third. She’d leave tech after five years — at which point she’d started writing about the industry, and her book.
It’s a book about the tech industry, sure, but it’s also a book about a 25-year-old woman growing into a 30-year-old woman. It’s about yearning and forming an identity and learning how our world works.
And it’s about sexism. The overwhelming majority of Wiener’s co-workers were men. The type of misogyny Wiener describes is at times shocking — clear-cut examples like “the colleague with the smartwatch app that was just an animated GIF of a woman’s breasts bouncing in perpetuity” and another who kept a list of “the most bangable women in the office.” Even when the sexism is more muted, it’s unrelenting.
We read about, for instance, when Wiener joins her first all-male team: “I wanted the men on my team to think I was smart and in control, and to never imagine me naked. I wanted them to see me as an equal — I cared less about being accepted by men sexually than I did about being accepted, full stop. I wanted to avoid, at all costs, being the feminist killjoy.”
And then, later, we read about her transition to the “feminist killjoy”: “I was the feminist killjoy. I did not pick my battles. I died on every available hill. I asked my coworkers to stop using words like ‘bitch’ in the company chat room. I bitched about being one of six women at a company of fifty. ... Sexism, misogyny, and objectification did not define the workplace — but they were everywhere. Like wallpaper, like air.”
Reviews have pointed to the fact that Wiener clarifies an industry — one that’s simultaneously ubiquitous and opaque — for people who don’t work in it. But so, too, does Wiener clarify what it means to be a 25-year-old woman moving through the world, and seeking something.
This interview has been lightly edited for length and clarity.
Anna Wiener: Hi, this is Anna.
Lena Felton: Hi Anna, this is Lena. I’m super excited to be talking with you today. As someone originally from the San Francisco Bay Area, I feel like I know —
AW: I noticed with the 415 area code. Where did you grow up?
LF: I grew up in Marin County, so I feel like I probably uniquely understood your book’s references to the crazy Tahoe trips and all the excesses of the Bay Area.
AW: Oh, yeah.
LF: I guess to start off, you end the book at the 2016 election, and then you provide a pretty short epilogue in terms of why you chose to exit the tech industry two years later. Can you talk a little about that decision?
AW: I chose to leave the industry in 2018 for a few reasons. I felt like it had just sort of run its course. I had also been writing about the industry, both putting together my book but also reporting on the industry more, and it just started to feel more incompatible for me. I wasn’t getting any pushback from the company I was working for, but I just felt sort of split between these two worlds and it didn’t feel good. Also, the book selling meant I could support myself financially without having a salary, so the timing was right.
But it was also this sort of feeling that I didn’t know what I was working toward anymore in tech. I had a sort of revival of my own ambition or had gotten excited about some of the policy work I had the potential to do around content moderation, but I was also encountering some institutional sclerosis, and I didn’t feel motivated to combat that. I think it was just a perfect storm of personal reasons — I guess it’s all personal, isn’t it?
LF: And I found the decision to make that all really condensed in the book itself was interesting as well.
AW: Yeah, I wanted to end the book at the election. I felt like this specific period had come to a close — or felt that something had come to a close, that the party was over. Of course, very little has changed in Silicon Valley; the change has been rhetorical, it’s been cosmetic. If anything, I think the industry has been emboldened to be clearer about what it is. But I felt at the time something had ended, and I do think it was a period of relative absence of scrutiny or a moment in which people weren’t criticizing the industry as much or looking at it as clearly, at least in the mainstream.
LF: I love the names you give to that era of tech. If you had to sort of name the era we’re currently in, what would you call it or how would you describe it?
AW: I know people have referred to this era as the “techlash.” I don’t know if I think that’s sufficient, only because there’s certainly increased criticism, but I haven’t seen a ton of change. I guess I feel like the way the industry has dealt with criticism has been really interesting and mirrors some of the political rhetoric we’re seeing on the right, in respect to responding to the media. I find it very alarming.
But if I were to give it a name, this new moment —
LF: It’s a hard one.
AW: Yeah, it’s definitely a hard question, especially for someone who’s attentive to language but also not great with speech. [Laughs]
LF: [Laughs] Oh yeah, I’m the exact same way.
AW: I feel like there’s a reason people like you and I go into writing rather than oration. I don’t know, it’s funny. I’m inclined to use some word like “reckoning,” but I feel like there isn’t the intended introspection or inclination to change that “reckoning” suggests.
LF: Maybe we’re at the precipice of that, but there haven’t been any real consequences yet.
AW: In a way, it’s almost like we’re seeing these companies become more themselves. So it’s more a hardening of sorts.
LF: Yeah, a doubling-down or something like that. It’s fascinating. I loved that you made the industry so much more clarified for the reader, especially as someone who isn’t in tech. I also love how you describe San Francisco — you pretty astutely mapped out how the city changed while you were there. I mean, you still are there. I was curious — do you feel like you fell for the city? Do you feel like you’ll stay there for a long time? How do you feel like your experience of it has shifted since you left tech and started writing?
AW: I have a lot of affection for San Francisco; I do think I’ll be there for the indeterminate future. It feels like home, I have community there, my partner is there and wants to stay. So we have a life that feels like our life.
You know, the city’s changing. It’s painful. New York is also changing; I was there last week. I grew up in Brooklyn, and it’s disorienting to walk around Brooklyn. It’s destabilizing to me. It’s unrecognizable in a lot of ways, and I try not to be nostalgic about that, because I know that change is sort of a natural progression. It’d be very strange if like my childhood was ossified.
But I think that San Francisco — I’m very fond of it. If anything, I feel like I wish I were more engaged with the city. I think there’s a lot I could do personally to be more closely involved with the direction it’s going. Documentation is just one mode of interaction. I will say that not being in tech — at first it was very jarring. I’ve described it to other people as having felt like the doors of power had closed on me. And I was outside. And there was a moment when this was very frightening to me, just given the political uncertainty and all of that. But I feel like I’m on my own feet. I feel more stable being outside those doors. I feel great relief, I have to say. I’m really glad not to be in the industry, and I feel really lucky to have found a way out.
LF: Do you feel like — just from your conversations with co-workers and friends — that a lot people are sort of thinking about that? Exiting at some point?
AW: Yeah, it’s funny, I think a lot of people are a little disenchanted, or aren’t sure what they’re working toward, what the end game is. I think that the industry — a lot of the people working inside the industry are really smart and deserve better and want better. And for whatever reason, these are the jobs that they have and that they need to keep and sometimes the work is interesting to them. I don’t want to discredit or discount that for people for whom that is true.
I think there is this feeling of what comes next, of how could this improve.
I think there’s quite a lot of doubt that that sort of change is going to come from the industry with its current incentives and organization.
LF: Well I just sort of loved how, at the end of the day, the book just charted you as a 25-year-old and having this yearning or desire to step inside that world, and then growing up in it and realizing five years later that your values are much clearer. And I feel like that’s not necessarily limited to the tech industry — a lot of people are finding themselves in their 20s and figuring out what matters to them. Do you have any sort of messages or takeaways from that for other women who are 25 or 27 or 30 and thinking about what they really want?
AW: Oh, I really try not to be a pundit or give advice, because I think that advice is so personal and so specific to someone’s situation.
And that I’d had the confidence to do something to change that or change things for myself. But I also understand that this industry does work for a lot of people, and I don’t mean to shame anyone when it is working for them.
I do think there are decisions people can make in the industry — some of them more ethically or morally sound than others. I do think at a certain point, if you are someone who has other job options and you aren’t on a visa and you don’t have dependents and you are, in many ways, free to move around the job market, I don’t know why people are working at Facebook right now. I try not to judge, but I also wonder why we aren’t seeing more movement.
LF: I do think it’s helpful to hear other people’s thought processes and all that. For me, throughout the book, I feel like the sexism of the industry was this sort of underlying thing that crept into so many different aspects of the book, which was kind of scary. I think we read all these stories about Silicon Valley’s diversity problem, but it’s a lot different to hear about those day-to-day interactions. I wonder if you were conscious of the extremity of some of the sexism you were facing as you were going through it, or if it was more about bucking up and accepting it and then engaging with it once you could look back?
AW: No, I knew that what I was encountering was — that a lot of the sexism I was encountering was not right. But I guess in my life I’ve been all too eager to make excuses for people who don’t deserve it, or to give people the benefit of the doubt to the extent that it’s to their benefit and to my detriment.
There’s this sort of bait and switch that happens in tech, where a lot of these companies tell stories about themselves being different, where they’re non-hierarchical and they’re anti-establishment and they’re doing things in a way that’s new or merit-based or creative in some way. But what that does is just creates space for all these structural problems to flood in under a different sort of artifice. So different hierarchies emerge, whether that’s the distinction between soft skills and hard skills and people being put into those categories based on qualities that have actually nothing to do with their skill set or contributions to a company.
I feel like I just wasn’t taking a wide enough view, I was sort of dealing things one by one. There was this situation — it’s not worth really going into, but I was not initially offered equity, and a man who was much less qualified than I was for the same role was offered equity right off the bat. It wasn’t until like 2017, when I was talking to a friend about this, and I was like, I think it’s because he had a computer science minor in college, even though we were both sociology majors. Or no, that wasn’t even it. He had some web-coding side project or whatever. And my friend was like:
I think this is a personal failure, that I’m always trying to look for the good in people and ignoring the structural explanation that would be clarifying in so many ways.
LF: I think that’s totally relatable. It’s a much more positive way to move through the world, I think, than being cynical.
AW: But it doesn’t serve anyone. It’s not a useful way to move through the world, and it can be quite frustrating and painful, at a certain level.
LF: Yeah, definitely. Well I loved your idea of an alternate Silicon Valley that would be matriarchal. What do you think Silicon Valley actually would’ve looked like if women had actually been at the helm?
AW: I don’t find that to be a particularly useful counter-factual, just because I think the sort of “Lean In” feminism, the “we need more female CEOs and executives” — that may be true, or that’s one way to look at it, but I think that’s very flattering to existing power structures. And actually what needs to change in the industry are the incentives and the emphasis on certain business models and hierarchies or non-hierarchies. So just putting more women in these structural positions isn’t going to actually change how the industry functions. I understand people who advocate for that, but I think there’s something quite resigned about it, and cynical as well. I’m not saying there should be no women CEOs, I’m just saying the whole system needs to change.
LF: Do you feel like you wrote this book for anyone?
AW: I tried not to think about that too much while writing, just because it felt overwhelming. You can’t write something for everyone. I wrote it thinking about my friends — what are the observations or jokes that my friends would find funny or interesting. How do I explain what I’ve been doing to people? How do I explain it to friends in New York? How do I communicate what I enjoyed and what I found horrifying? How do I communicate this data analytics software in words that won’t make them want to fall asleep?
At some of the readings I’ve done, women have come up and said, “I work at X company or W company and what you’re writing really resonates with me, and I’ve found that really meaningful.”
I wouldn’t have known that that was who I was writing it for, though it’s important to me that I get it right for that audience.
LF: And what was your most surprising discovery about yourself through the process of writing the book?
AW: That’s a good question. I think my preference for a sort of detached, observer position. I’m so much more comfortable on the periphery of my own experience, and I think writing a memoir really challenged that. It’s not the most personal of books, which I’m aware of — I don’t know if that works for the book or doesn’t work for the book, but my hope is that it did. I think just trying to figure out where those lines were for me and when does disclosure make a book better and when is it worth making myself uncomfortable, and when is it worth withholding a little bit. Not just for myself, but for the reader.
LF: It’s true. I think that’s the struggle at the heart of memoir, which is that you have to be detached to the extent that you can make a narrative and a story out of your own life. So it’s definitely a hard balance. But I really loved the book, and I’m going to share it with all my friends who are in tech now.
AW: Thank you, I hope they like it. When I was Googling you earlier, I saw that you graduated just a couple of years ago, right? I’m curious if things have gotten better — if your friends who are in tech are experiencing something different. Because it moves relatively quickly, I think.
LF: Yeah, a couple of my really good friends are in tech. One of my best friends just joined a start-up, and for her — she’s an engineer. She’s always the one woman engineer. At a start-up, I think things are really different — interacting directly with the CEO, wanting him to like your ideas, etc., as you talk about in the book. But yeah, from what I hear, it’s so male-dominated. Maybe there are less overt sexist jokes and all of that, but all of the women I know feel pretty alone.
AW: I hate hearing that.
LF: But I think it goes to show that you can’t just put a couple women up in high positions and think it all gets better.