Anna Wiener on Being a Jewish Woman ‘Outsider’ in the Tech World

The writer talks about her new memoir, "Uncanny Valley," and what scares her the most about the tech industry.

Midway through our conversation, author Anna Wiener tells me, “Tech culture is just incredibly goyishe. I don’t even know where to begin with that.”

We had been talking about her experiences as a Jewish woman in the tech industry in Silicon Valley, where Wiener always felt like an outsider. Her debut memoir, Uncanny Valley, is “written from the perspective of an insider who never felt fully accepted, or fully like an insider.”

“In talking to my friends about this, especially the Jewish ones, people are like, ‘Oh, you feel like an outsider in your own culture? How unique,'” she jokes sarcastically. “I do think that there’s a long tradition of people on the periphery of their own experience who are Jewish.”

Uncanny Valley is a gripping and engaging read, and as I wrote in our most anticipated books of winter 2020, a searing indictment of start-up culture and “tech bros.” It’s meant for those who work in tech and those whose lives are impacted by tech (so, all of us). And I can’t recommend it highly enough. Wiener moved from New York to San Francisco in her mid-20s, ended up at a data start-up, and remained in the industry for the next five years. Uncanny Valley traces her experiences, but as she emphasizes over the course of our conversation, the book is about much more than just her experience. It’s the experience of so many women and others in the industry who are not CEOs or venture capitalists, but the people creating — and supporting — the technology that is fundamental to our world.

I chatted with Wiener about all things Uncanny Valley — from advice she would give to someone looking to work in tech, to what is currently giving her hope.

This interview has been lightly edited and condensed. 

Where does the title Uncanny Valley come from?

The title is a term often used in robotics to describe the feeling that a person has when a robot becomes more and more lifelike. So as it approaches life-likeness, there’s a dip in your affinity — there’s a valley in the way that a person feels toward it. People tend to feel fondly toward robots that have lifelike characteristics, but then as they start to really get closer to something that feels real, there’s a sense of revulsion or horror. That is what’s referred to when people talk about the “uncanny valley”: you find yourself in that emotional response.

One of my favorite parts of the book was when you write about the infinite scroll and how our brains are a “trash vortex” as we become addicted to the internet. How do you navigate your relationship with the internet and social media?

Oh, it’s worse than it’s ever been.

Oh no!

I know. Well, it’s funny because I’m now writing full time and I don’t go to an office or even a co-working space, so I don’t have any of the corporate communication software in my life anymore. Which is a blessing; I hear my boyfriend’s Slack go off sometimes, and I’ll have an emotional response. It’s very Pavlovian. Social media now is a way for me to feel like there’s some activity in the room, which is really bad! I should just be leaving the house and taking a walk. But instead, I’m looking at Twitter.

It’s tough because I am writing about the tech industry still, and a lot of people in the tech industry hang out online. So there’s a lot of material being generated, and a lot of, for lack of a better word, tech being generated from people in the industry, that are all on the internet. A big part of my research is trying to keep tabs on what people are talking about, and where they’re talking about it. I’m trying to be more deliberate about what I’m doing, but I still end up spending a lot of more time online.

You briefly discuss the sexual harassment you faced in the industry, writing about a co-worker who once told you he loves dating Jewish women. Did you encounter moments like that often? 

Being Jewish hasn’t been really important to how I’ve experienced my analysis of the industry, and my critique of the industry. That particular scene — I just thought it was so strange. I didn’t actually feel particularly Jewish in that moment. I just felt like, This person is so weird. What a thing to say to someone. There’s a part of me that [thought], Should I think this is a compliment? And I think it was intended as a compliment. The whole thing was just so strange.

Does your Jewish identity influence your writing at all?

I started writing this book in 2017, for the most part. I’d written that n+1 essay that it came out of. And after the 2016 election, I’d never felt more Jewish in my life.

People were talking a lot about fascism, and people around tech, who were talking about tech, were starting to talk about fascism. As I was finishing the book in 2018/early 2019, there were whole sections that I just had to remove that were about people in tech who seemed to be developing fascist sympathies.

I had a running joke with friends — mostly Jewish friends — that my book was going to end up being shelved in the Jewish American literature section. Because I suddenly felt acutely aware of my own Jewishness, how that informed my work, and how I was feeling about certain things happening in the industry post-election.

On a totally different note, I noticed you don’t name any brands or companies throughout the memoir — I assume that was a conscious decision?

Yeah, and that’s just a stylistic decision, for the most part. I do name a couple. I have a couple proper nouns that I really struggled against, but eventually let them in. One of them is RipStick, another is Michael Jackson. I just couldn’t think of a better way to describe these things without it being distracting.

It’s not hard to find out where I worked, and it’s completely within bounds for me to talk about where I worked. I just felt like the story is really more about a culture and a system. And I’m not coming at it from a place of contempt; I’m not trying to write a tell-all about any particular company or person. It seemed like it wouldn’t really matter; like in five years, I don’t know if any of these companies will exist. I mean, in 20 years, will it matter? A lot of the experiences I had were pretty common, especially for women. So I think in a lot of ways, you could sort of just sub in the name of many other companies.

If a young woman graduating college now asked you if she should pursue a career in Silicon Valley, what would you say?

I would say do a lot of research, talk to a lot of people. I would probably say, how can I help you? I think there’s a range — some companies are a lot better to work for than others, and it can often be very hard to find those companies because there’s so much rhetoric and so much marketing and a lot of hype that can be a little bit noisy, especially for someone starting out.

What do you think is the biggest misconception about Silicon Valley, or working in tech in general?

That any of this is inevitable. We’re all treating this as inevitable — and by this, I am sort of gesturing broadly to toxic workplace culture, optimization culture, rampant misogyny, and racism. I think that this can change. I really do. And I’m optimistic, weirdly, about the capacity for change. I think people really have to want it, and they really have to start interrogating the power structures in the industry and the incentives of industry. I think we’re stagnating a little bit by believing this to be immutable.

I saw you tweeted about how this book will “probably make me totally unemployable in the ascendant industry of my generation.”

[Laughs] Oh my god, my tweets are gonna make me unemployable!

I’m sorry to quote your tweets back at you! What do you think the reaction to this book will be within the tech world? Or, what do you hope the reaction will be?

People who are sort of average employees, rank and file employees, that’s the reader that I’m hoping to reach. I hope people see themselves in it. I found it very gratifying to get emails from people from other companies who’ve read some of my writing about the tech world and have identified with it. I really do think that I’m like the least interesting part of the story. And my hope is that it’s a book about a time in a place in a culture. It’s more a portrait of an era than it is of my life; my life is as interesting as anyone else’s life. I hope that it resonates with people who have been in San Francisco around the same time that I have, who have seen how [tech has] changed the city and how the industry has shifted.

I don’t know that people who are founders or venture capitalists… it’s not flattering to a lot of people in positions of power. And my hope would be that maybe they would start thinking a little bit more about the experience of their employees. A lot of the literature geared toward people in executive positions or more powerful roles is management literature; it’s operations oriented, [and has] very little to do with the day-to-day experience people have in the industry. It’s a really tight-knit world, and I think people expect a certain amount of loyalty. And that’s part of the promise of the industry, I think — that doing something disloyal, not being down for the cause, so to speak, is considered traitorous.

What scares you the most about tech? What gives you the most hope?

What scares me the most is there doesn’t seem to be a ton of accountability or transparency. The power relations really makes me nervous. But on the flip side of that, what gives me hope is some of the nascent worker organizing and people from inside these companies starting to talk more publicly about what they’re doing and starting to push on leadership. Collective action is exciting, and employees of these companies should have a much bigger seat at the table in decision-making, and it seems like people are starting to realize that. The specific issues have been really polarizing internally at these companies, but on a whole, just a movement toward that can be really meaningful and potentially change the trajectory of the industry.

Image of Anna Wiener in header by Russell Perkins.

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