Why Normal People Want to Work in Silicon Valley

Anna Wiener’s new memoir, Uncanny Valley, tells the story of a regular person under the spell of disruption.


“It was easy to get me to want something,” the New Yorker columnist Anna Wiener confesses in her tech-industry memoir, Uncanny Valley, out today. She left publishing for her first tech job, at a New York ebook start-up, in 2013, and almost immediately fell for the industry’s charms. She moved to California to work at a mysterious data-analytics company, then an open-source software platform that had just been through a famous scandal.

The book about the four years that followed has already been widely praised, and it was regarded as a “most anticipated” for months, thanks in part to the thrill of its insider gossip—any reader could spend weeks guessing at which companies and CEOs and whistle-blowers are referred to obliquely in its pages. Slate’s Dan Kois wrote a guide to the book’s proper nouns, and confessed that he spent “forever” trying to identify the friend of Wiener’s who found out that he was a billionaire while the two of them were eating lunch, before finding his name in the acknowledgments. (It’s Patrick Collison, the CEO of the payment processor Stripe.)

There are plenty of abuses of power and absurd anecdotes in Uncanny Valley—a manager forcing a job applicant to take the LSAT on the spot stands out—but the strangest thing about the book is how well it makes Silicon Valley look like a mirage that anybody could be taken in by. In particular, Wiener dedicates significant space to her enchantment with “the boys”—the overconfident 20-somethings who were “ambitious, aggressive, [and] arrogant” but also “focused and content,” who both bolstered her spirits and made her feel old. They were not lonely. They were “clean-shaven and had good skin.” The life they had was one of promise and purpose.

Wiener was a customer-support manager, not an engineer or a founder, so she always found herself a little bit peripheral to the big-dreaming action, but she was still present for the glamour and the gold rush. She wasn’t a CEO giving Beyoncé millions of dollars in stock to perform at a party—she was an average employee, interested in finding fulfilling work and worrying less about money than she had been. “I would allow myself to be taken care of,” she decided at one point. “As if I had done something to deserve it.”

I spoke with Wiener over the phone the day before her book’s release. This interview has been edited for length and clarity.

Kaitlyn Tiffany: The aspect of the book that really grabbed my attention was the fact that you weren’t this stereotype of a disruption-hungry bro who wants to make a billion dollars, but you could still be taken in by a lot of the promises of Silicon Valley. What made Silicon Valley so seductive to you?

Anna Wiener: This is a part of the book where I hope the personal story illuminates the structural story of Silicon Valley. For me, the things that were exciting about tech had a lot to do with the fact that I had graduated into a job market that had been affected by the recession dramatically, and I had gone into an industry that felt like it was shrinking. There was a feeling that the sky was always falling.

In tech, it wasn’t so much the products that I was excited about. I wasn’t like, This is the utopian frontier. It was more like, Here’s an industry where there’s a lot of opportunity, there’s a lot of money, there’s a lot of excitement. More than that, there’s a sense of momentum and a sense of freedom for even rank-and-file employees at a start-up. There was something really gratifying about that. It sort of affirmed these stories that I had been told, how I could do something in the world that had an impact. I had always assumed I would feel useful in some sort of way. And in tech, you just feel incredibly useful, because you’ve worked incredibly hard and you’ve been sold a lot of stories about the importance of that work.

It was just that feeling of momentum and of latitude. This industry was only going to grow, and you were only going to find more opportunities for yourself. It just seemed so anomalous in that economy.

Tiffany: Early in the book, you say that what hooked you was “the eagerness and optimism” and “the boyishness.” What was so charming about the boys?

Wiener: As a self-conscious, sort of shy, professionally awkward [woman], for me in my 20s to encounter that young male confidence—I wanted it. I wanted to feel confident; I didn’t want to be insecure. I wanted to feel like the world appreciated me, and that seemed like a pathway [toward] feeling useful or having the feeling of having found one’s place.

Tiffany: How did you walk the line between being empathetic toward the people who were part of your life at the time and also being very critical of a lot of the things that they were doing or that you were doing?

Wiener: I have heard the feedback that my capacity for empathy is both my best and worst trait. I do think that I tend to forgive and excuse people who are beyond the threshold of that being appropriate. But in the case of the book, for me it was very important to portray people as people. In a lot of ways, what was happening in Silicon Valley had more to do with a structural story than an individual one. And a lot of people were behaving in accordance with their structural position.

But then structural explanations can absolve people who should not be forgiven. There’s a tension there, always. [Empathy is] politically a complex mode of relating to people. In Silicon Valley, it was something that people tried to learn, which feels so cold to me, to think of that as a skill to be learned. Part of the problem of Silicon Valley and the start-up world is that they don’t treat people like humans. They either tend to be incredibly reductive and cruel or overly flattering. My hope is, by portraying people with an ambivalence that is emotionally true to my experience, that there is some utility in that, in terms of widening the conversation about who’s actually behind this industry.

Tiffany: In the book, you talk about the intellectual culture of Silicon Valley and how it’s very similar to internet culture—a lot of people doing hypothetical thought experiments. That seems like part of the empathy problem, too.

Wiener: It’s a really impoverished intellectual culture. If you think about who the intellectual figureheads are—I’m teetering on the brink of naming names and then wondering if that is uncouth—it’s like economists and venture capitalists and founders. The intellectual culture is very flattering to power.

This ideas culture, this thought-experiment, contrarian culture—I find it very embarrassing. I think it’s really anti-intellectual; I think it’s ahistorical. When you think about human knowledge, it builds on itself, it grows. Academia, as flawed as it is, is a project, a slow project that has deep roots in the past. And tech is an industry where the past is rather inconvenient and there’s this sense that everything is unprecedented. The intellectual culture also reflects the business model, and I think both benefit from being a little ahistorical and a little anti-academic, anti-intellectual.

Tiffany: You profiled Ellen Ullman a few years ago—she’s really the original great Silicon Valley memoirist, and has talked a lot about how tech needs to be more human and more diversely human. Do you agree with her that everybody should learn how to code, to bring the general population and the tech industry into more of a shared language?

Wiener: I love Ellen Ullman; I think she’s brilliant. I think she also knows that’s only one path. I don’t think she would say that’s the solution. I think what’s behind that sentiment is this sense that technology is a black box and people don’t understand how it works, and there’s a power relationship there, where people building technology have power over the people using it. One of the things I learned working at this analytics start-up is just how much the people behind the curtain can see, and how little control the people who were actually using these products had over their own experiences. The problem that needs to be solved there is one of transparency and autonomy. Learning how to code is one way to approach it. But it’s also about education and leveling out that power dynamic.

Tiffany: Do you remember a moment when the whole thing felt really fun? Or a moment when it really stopped feeling that way?

Wiener: I think the disillusionment was a slow burn and I really did try my best to stave it off, because I had bought in so hard at the beginning. I was engaging in a lot of self-delusion to resist that disillusionment. My first six months at the analytics start-up were just so intoxicating. I was trusted to do important work and that felt amazing.

When I was trying to recruit my friends to work for the company, I felt such great pride representing the company to other people. And now in hindsight, I feel very embarrassed, because it’s clear I had just become this mouthpiece. [At the time,] I felt like people looked at me and associated me with this thing that was taking off, and it was this shimmer of affiliation or something.

Tiffany: Being an adult, working a rote job, and having no expendable income is really lonely and monotonous and degrading. I think maybe anybody could be charmed by an alternative to that.

Wiener: Oh, absolutely. A lot of the people I worked with were incredibly smart and really talented. And a lot of them did not have what you might consider a traditional background for a tech job or an engineering job even. A lot of people were self-taught after doing something else. This is a structural story, because you have a lot of people who in a different economy would be doing any number of other things.

I worked with people who had Ph.D.s in musicology or composition and people who had library-science degrees. I worked with a woman who had been a practicing lawyer in Canada. These are people who, if there were a more robust economy—and there were a lot of people my age who were similarly affected by the recession—they would have done anything else. There were a lot of people who in another time would not have chosen this as their first choice.

Tiffany: Is there anything you want people to keep in mind while they’re reading the book?

Wiener: I would just say that I’m hoping that other people in tech read it and they relate to it in some way, and that it articulates an experience that I believe to be common and not just my own. I hope it opens up space for more writing like this, by which I mean writing about tech from the perspective of someone who’s just an average employee and not an executive.