Anna Wiener

Anna Wiener at her home in San Francisco, photographed by Cayce Clifford.

The first great book of the new decade has arrived and it is, presciently, about the perils of the tech industry. At 25, Anna Wiener traded her entry-level job at a New York literary agency for the hubristic utopianism (and free snacks) of Silicon Valley. Seven years later, she's written a withering and insightful memoir about her time there, "Uncanny Valley," which comes out today. We caught up with Anna, who lives in San Francisco and now writes for The New Yorker, to talk about the book, the industry that inspired it, and Mark Zuckerberg's smug fashion sense.

Anna, congratulations on the book! How are you feeling?

Thank you! I’m curious who its readers will be, and what they’ll make of it. I’m hopeful that people in tech will want to read it. It’s weird, I have a finished copy on my desk, but it doesn’t feel real that it’s done. The material is still alive for me. There’s still so much I want to talk about and write about, with respect to this world.

Do you have any plans to celebrate today?

I’m doing a reading at the McNally Jackson in Williamsburg, and a Q&A with my friend Molly Fischer. After that, I’m hoping to meet up with friends—I don’t have a big plan.

The reviews are pretty much uniformly stellar. Are you surprised by anything that’s been written so far?

It’s just astonishing to me that people are giving so much time to a book that I wrote. I can’t get over it. It’s such a privilege.

Why did you choose to write a memoir as opposed to say, a collection of essays or even a novel?

I really wanted to write something that felt true to my experience. I don’t know that the material lends itself to an essay collection, where each essay would put forth a question, thesis, theme, or idea. I didn’t want to write fiction because I felt like no one would take it seriously or believe me, especially as a woman and non-engineer. I was worried it would be misunderstood, and dismissed, as satire.

In the book, you note that the Internet has led to a lot of “bloated,” over-researched writing. How did you avoid this pitfall yourself?

I tried to focus on material from my own life—emails to friends, text messages, photographs—rather than Google broadly or read a lot of commentary and news stories. I wanted to be protective of the material, and not let too many other voices or ideas flood in. I do wonder if my obsessive cataloging and list-making is its own form of bloat, though. I don’t think I’m immune to the internet’s influence.

You also observe how Silicon Valley tends to play fast and loose with the English language, from sloppy grammar to empty business-speak to just really dumb portmanteaus. Why is that? Do you think it stems from a general disregard for any language that isn’t code?

That’s a really interesting question. I don’t think there’s a disregard for languages that aren’t coding languages, though some people might exhibit a certain indifference. I think what spoken, or written language has in common with code is that each has its own logic, right? Each has its own rules and structure and restraints. Code has a computational logic, and provides a really clear sense of right or wrong, working or not working. When something is broken, you know it immediately. Natural languages can obfuscate and circumvent and be ambiguous and vague, and I can see that being really infuriating to a certain type of person. That said, I do think that jargon and euphemism can serve as a cover for thoughtfulness and intent, and can put a gloss on systems or behaviors deserving of great scrutiny.

Even for readers who’ve never stepped foot in Silicon Valley, your book is relatable, especially from a consumption standpoint. At one point, you compare your online browsing habits to “careening across the Internet like a drunk.” What is your relationship with the web today?

I’m definitely still reckless in my Internet behavior. I wish I had the self-discipline of someone like Jenny Odell, whose book, "How to Do Nothing," I loved. But I will say that between the death of Google Reader, the consolidation of media, and the rise of ad-driven platforms, my internet feels much smaller these days. I’m also very lucky to be doing work now that I really enjoy, so my time does feel more focused. I feel less that I am sleepwalking through my life.

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“There’s still so much I want to talk about and write about, with respect to this world.”
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Your writing is so funny and caustic, even the smallest detail doesn’t escape your gimlet eye. There’s that great line where you describe a (probably Allbirds) sneaker as, “a child’s drawing of a shoe.”

Thanks! Yes, that was a side-eye at the ubiquitous gray Allbirds sneaker. There are a lot of brands right now, like Everlane and Alex Mill, that are offering simple basics for everyday life, where the life in question seems to take place mostly at the office. There is a certain strain of thought, perhaps best summarized by Mark Zuckerberg’s closet of gray t-shirts, that privileges this homogeneity, or uniformity. The idea is that a uniform frees your mind to think about more important things. This might work for some people, but I find it boring, and also I think there’s something a little gendered about the dismissal of fashion.

All that said, I just––as in, twelve hours ago––learned about the interpretation of mass generics as a response to anxiety about mass surveillance, a linkage proposed by K-Hole, the group that coined the phrase “normcore.” Kate Crawford, a media theorist, spoke on this––a “fantasy of disappearance”––at a conference hosted by Rhizome several years ago, saying disappearance, or a certain erasure of individuality, “has become cool at the very historical moment when it has become impossible.”

How much is the tech industry responsible for our culture’s current fixation with productivity and efficiency?

I think tech is sort of a steroidal form of capitalism. The tech industry makes tools to quantify productivity, so there’s a particular investment in that value system. I also think the idea of productivity being morally superior is a story people tell to justify their own decisions and lifestyles. It’s very flattering to the greatest beneficiaries of capitalism.

You mention a lot of Silicon Valley companies and luminaries in “Uncanny Valley,” but none by name. Why did you decide on this blanket anonymity?

Mostly, it was a stylistic decision. I just felt like it didn’t matter who the companies or executives were, specifically. In terms of the things I was writing about, most of them were interchangeable and generic to the industry. My hope is that the naming scheme highlights what the companies actually do, and what their role in society is, while giving the book a sort of dreamlike quality.

You had a ring-side seat to some of the biggest issues plaguing the industry, from surveillance culture to misogyny. Do you ever wish you’d done more at the time or in a particular instance?

Yeah, in some situations, of course. It’s tough, because I was such a low-level employee––it’s not like I had a ton of institutional clout. A lot of what needs to be fixed is structural, and requires collective, not individual, work.

Do you feel guilt?

I feel foolish. I feel some shame. I do feel that there was a collective responsibility that was fumbled.

After reading about the burn out you describe, one might assume your next move was to Vermont to teach English literature. Why did you decide to a) stay in San Francisco and b) become a tech journalist?

All the qualities of the culture that interested me when I moved out here are still interesting to me. All the ingredients for human drama are here: ambition, disappointment, failure, betrayal, moral quandaries, more power and wealth than anyone should have, or know what to do with. I no longer want to be a participant in the culture. I don’t think I’m very useful inside the machine. I want to observe and process and communicate what’s going on here, culturally, and my hope is that this can be useful.

The question I was constantly asking myself when I worked in tech was, “Is this useful? Is what I’m doing useful?” Based on my salary allocation, the world was telling me it was. But I did wonder, all the time, why I wasn’t professionalizing in something that was actually meaningful to other people. Maybe I should have gotten an advanced degree in education, and taught English in Vermont. My hope is that my writing on Silicon Valley is useful. I mean, not to overstate my…

Don’t be modest.

[laughs] I think what I’m doing now is more useful than what I was doing before. And the moment it becomes not useful is when my writing becomes a mouthpiece for the industry. I never want it to be that.

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“I don’t think I’m very useful inside the machine.”
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From a journalistic standpoint, what issues are interesting you these days?

I think my book is sort of a CliffsNotes to my interests. I feel like I could take any paragraph and blow it out into 6,000 words. My general feeling is that we’re in a moment where we’ve lost sight of the fact that tech is still a young industry. I want to know what might happen if we stop treating everything as inevitable, what other forms of business models or organizational models might emerge. Can power shift, and how?

I’m also interested in what shape this sort of newfound political power is going to take. There are a lot of young people in Silicon Valley who are set up to make a ton of money in the next decade. I want to know what they do with that. I’m not interested in what their vacation homes look like. I suspect we’ll see a lot more tech figures move into politics, run for office. That’s intriguing to me not only because it’s another form of hubris, but it also highlights some parallels between DC and Silicon Valley.

What is good about the industry? What gives you hope?

[laughs]. Cue five minutes of silence. There are a lot of smart and talented people here. They’re not necessarily the people running the companies. They want and deserve better. I put my hope on them. I know it’s a little abstract.

And there are a lot of things we haven’t tried yet. We haven’t tried collective ownership or transparent data collection practices or smart, sensible regulations.

In the spirit of the new decade, do you have any specific predications?

Asking me for tech predictions is like asking me to do your Tarot reading. I’m totally in over my head and will just make some sh*t up.

When you worked in tech, one of your interview questions was, “Describe the Internet to a medieval farmer.”

[laughs]. It’s such an absurd question. When you hear it, it’s horrifying. But it works! It actually does tell you how someone explains abstract and complicated concepts.

So, last question—how would you answer that question?

I guess I would describe it as a…God, even the language we use to describe the Internet would be so abstract in the 15th century… a collection of archives of human knowledge that’s being rewritten every day? But that’s too utopian. Wow, I really thought leaving the industry would exempt me from ever having to answer this question again. I would say it’s a communications tool and a catalogue of… rich media? You know what, I’m going to decline to answer. [laughs] My unwillingness to answer this is probably as indicative as anything of my unsuitability for this industry.

Keep up with Anna

Twitter: @annawiener