Anna Wiener Looks Straight Into the Uncanny Valley of Tech

Photo by Russell Perkins. Art by Mark Burger.

Anna Wiener’s debut memoir Uncanny Valley, out January 14 from Farrar, Straus & Giroux, is a thought-provoking, personal, and often surprisingly poetic critique of the far-reaching influence of the tech world. In her 20s, Weiner, now a contributing writer to the New Yorker, struggled to find a place for herself in a publishing industry that felt steeped in hierarchy and dusty tradition. When she began working at an e-book start-up in New York City, the early optimism and financial rewards of tech seemed freeing. When she moved to San Francisco for another tech job, Wiener quickly found herself in a world of young millionaires, body optimization, and extravagant trips to Michelin-star restaurants and Lake Tahoe resorts. But there was a dark side to the excess, which Wiener chronicles with care: the rise of the NSA, mass surveillance, sexual harassment in the workplace and online, and 25 year-old CEOS are both very smart and slightly sociopathic. 

Wiener’s narrative is by turns funny, informative, and a perfect time capsule of a rapidly changing city. Her descriptions of burnt-out hippies and homeless people living in tents along Haight Street are just as compelling as the first-person peeks she gives us inside global tech companies whose offices contain rooms designed to mimic the Oval Office. Wiener gives us a look at what it’s like to bee messily human in a digital world—one that once upon a time felt limitless.

Interview spoke with Wiener about her early days on social media, data collection and surveillance, pervasive sexism, and whether empathy can exist online. 


ROYAL YOUNG: Let’s talk about the start of social media and the internet as we know it today. I feel like there was a weird sense of innocence in the beginning. 

ANNA WIENER: I think social media has always been touted as having utopian qualities of connection, democratization, and the erosion of gatekeeping to allow all voices to rise up. I’m not a student of social media. I’m someone who experienced it and is of that weird micro-generation I think we both belong to, where we kind of came of age with the internet but can remember a time before it. There’s a little bit of skepticism, but you’re also fully surfing the digital wave. I actually have very fond memories of early social media.

YOUNG: Me too.

WIENER: Something went haywire. The first real social network I participated in was LiveJournal. As a fellow New Yorker, this may be embarrassing, but I was really excited about being part of the ska punk community. So, I would meet these kids at the Punk Temple in Bensonhurst or the Knitting Factory when it was still in Tribeca. I met quite a few friends in that scene on LiveJournal and never thought twice about it. It wasn’t until I started working in publishing that I began to understand a platform like Twitter or other social media as a marketing vehicle. I realized, oh, this is not just a place where people are selling commodities, but selling themselves as commodities. 

YOUNG: You write about experience versus owning, and how our generation prefers to pay for things that aren’t permanently ours. 

WIENER: Millennials are often blamed for the death of what are now considered luxuries. The actual story is more about a sense of precariousness, a certain transience and a lot of uncertainty around job opportunities and debt. In terms of my own experience, I think a lot of these services are aspirational. They take advantage of the fact that a lot of people do live with a sense of financial insecurity. To me, they seem like they circumvent the root problem, which is what Silicon Valley is great at. 

YOUNG: The words aspirational, inspirational, motivational are ones we hear all the time now. And it’s like, whose aspirations are these?

WIENER: Right. It’s so funny, when I first moved to San Francisco, I felt like I had inhabited someone else’s life. I had put on the costume and taken over some script for a successful person in tech. It was compounded by the fact that by chance the first place I stayed was an Airbnb owned by one of the founders of Airbnb and getting into Lyfts at the time when they still had those ridiculous pink mustaches on the grill. Just feeling like I stumbled into “It’s a Small World After All” but for start-ups. 

YOUNG: Early in your time in San Francisco, you’re at a party and someone is talking about buying property in Oakland and says it’s “too dangerous.” But what are the differences between the dangers of, say, gentrification versus massive online spying and data collection?

WIENER: I don’t think they’re as distinct as they would seem at first glance. The tech industry is pretty homogenous and that has an effect with how people interact with the Bay Area and each other. I don’t want to conflate too many things together. The real estate market in the Bay Area has been fucked up for decades. A lot of people in tech have been beneficiaries of California’s housing crisis. A lot of people in tech have exacerbated it, but it’s not just a tech issue. 

Data collection is not terribly far away from that. Not necessarily the company I was working for, but others that would be more clearly classified as surveillance companies. Who is most vulnerable to surveillance? Who stands to lose the most when we have a surveillance-oriented society? It’s hard to answer specifically, because I feel like we are talking about so many things braided together. 

YOUNG: Yeah, it’s hard because I think technology has braided all these things together and is so all-encompassing. You can get an Airbnb, buy a house, shop for anything, look at porn, go on social. It’s so embedded in everything we do in our everyday lives, it’s hard to see where it stops and begins. 

WIENER: I agree. That’s why in writing the book, it was important for me to capture a sense of place—San Francisco specifically. For me, I couldn’t write a book just about the internet because I think it’s inextricable from the physical repercussions. 

YOUNG: Do you think that’s one of the reasons so many of the internet companies you write about had such a focus on interior design in their offices? It’s a way of bringing their online personality into a touchable incarnation. 

WIENER: That’s a theory I have, but I have no way of knowing if it’s bullshit. That because it’s so intangible, and so much of the labor is intangible, there’s a physical environment that’s designed to offset the psychological burden of working on things you can’t touch but have huge influence. 

YOUNG: Where do you think tech’s fascination with authenticity—but wanting also to commodify it—comes from? Like, how an e-book company you worked for supposedly wanted your literary expertise, but didn’t want to do a book club. 

WIENER: This question of expertise is a really important one, because expertise doesn’t have the same cache in Silicon Valley as I think one might hope it would. There’s a sense that this is all unprecedented. It’s almost as if entire institutions and regulatory bodies don’t apply. There’s also a question of, can the social and cultural capital transfer over to a digital space? Especially when these digital spaces are so homogenous in their design. There are very limited ways someone can behave on Facebook or Twitter or Instagram, and that seems by design. Platforms have their own incentives and they’r very specifically oriented towards monetization.  

YOUNG: Do you see that ever changing?

WIENER: I think it’s unlikely to change unless the business models of these companies change, and in many cases that would mean the complete collapse of social media. 


WIENER: Well, think about a social network that is not oriented towards engagement, that is not an ad network, is not trying to encourage constant return to the platform and constant content production on the part of the user. Or think about what it would look like for Amazon to run an ethical, responsible business and the amount of money that would take to moderate. 

YOUNG: Do you think we as Americans have sacrificed other qualities for speed or convenience? Like, access to all our personal information so that we can get an Amazon package overnight?

WIENER: I think people are making trade-offs all the time. A lot of the issues with tech are not unique to tech. Tech just amplifies, exacerbates, and accelerates them. This isn’t new. This is American capitalism.  

YOUNG: How do you think the lack of diversity in the tech world shapes it? 

WIENER: The question is always: Do those people have a voice inside the companies? People have been talking about abuse and harassment inside these companies and online—discrimination, racism, and sexism—for years. It’s not even unique to this wave of tech. But it’s always a question of who is listened to and who has buy-in from people in senior positions. It’s a question about power and a fear and an unwillingness to relinquish power. 

I went to a women in tech conference in Phoenix. Until then, I had sort of internalized that hierarchy and thought if you had a higher skill set, you would be more valued in the industry. But despite the industry’s obsession with meritocracy, you will see that it’s usually women and other underrepresented minorities in tech that have to produce the credentials. 

YOUNG: I loved how all the male CEOs at that conference were like, “Just work harder. Don’t ask for a raise, trust in karma.” 

WIENER: Yeah, karma, that’s their business model. That conference was my first time being around women in engineering, who were highly skilled and respected in broader communities but were running up against the same problems I was, which was pervasive sexism. That shouldn’t have been a surprise to me, but it felt like another way the industry had failed to live up to its own narratives. 

YOUNG: Do you think feeling is viewed as a weakness in tech?

WIENER: There’s a lot of conversation around empathy, but it’s gotten so far away from what empathy actually is. It’s become another skill you can learn by maybe reading a Medium post about ways to build empathy in a certain amount of hours. One of the things I found so funny about this is that data can so easily be manipulated to tell a story, it becomes another narrative form. To learn and to tell stories about how people behave online is fascinating. But even this, which can be considered a very fact-based, unemotional data-driven mindset, is just as subject to narrativization. 

It’s been very weird to be doing interviews about the book and have people ask me questions about the tech world and where it’s going and what should be done. I don’t even want to give people advice on what to wear. I don’t want to become the thing that I’m criticizing and think is dangerous, which is someone who feels entitled to push their vision of the world into fruition.