Anna Wiener Dissects the Brain Rot of Big Tech in Her Searing New Memoir
In her mid-twenties, Anna Wiener was working a dead-end job in book publishing when she dropped everything and headed west to Silicon Valley, land of unbridled ambition, surreal excess, and multi-million dollar recklessness. She joined a data analytics startup, where she gained a front row seat to the amorality and extravagance of the new digital economy. What has emerged from those experiences is Uncanny Valley, a hyper-detailed, thoroughly engrossing memoir about her coming-of-age in Silicon Valley during the early years of the startup boom.
Yet Uncanny Valley is so much more than a memoir—it’s a vivid, unflinching portrait of a changed San Francisco, a onetime haven for artists and dreamers now dangerously in thrall to the capitalist chokehold of tech monoliths. At the intersection of exploitative labor, entitled men, and ungodly amounts of venture capital, Wiener bears witness to the fearsome future as it unfolds. Esquire spoke with Wiener, now the tech correspondent at The New Yorker, about mythologization of male founders, selfhood in the workplace, and legal accountability for Big Tech.
Esquire: What was your approach to collecting information about this period of your life?
Anna Wiener: When I moved to San Francisco, I was twenty-five and very lonely; I didn’t have many friends in the city. What little down-time I had, I mostly spent emailing with friends in New York. I have all of these long emails to friends that were actually incredibly helpful in writing this book, although quite cringeworthy. Same thing with text messages.
If I hear a piece of dialogue that’s funny to me on the street or if I witness an interaction, I’ll write it up in an email, send it to myself, and put it in a folder. I had this folder called “Notes To Self” with several thousand emails that were all just snippets.
These were my resources, and about halfway through the writing, I interviewed former coworkers and colleagues. I just wanted to compare notes. Also, there are documents. I had to write a performance review for myself at the end of one year; I wrote this long performance review and showed it to my mom, who said, “Don’t put all this in writing. They’re going to fire you as soon as it sounds like you’re vaguely interested in legal action.” I have this thing I never submitted, but it’s a clear document of my experience, written from that moment. I just had to pull everything together.
ESQ: Were your former coworkers generally excited to participate, or were they at all fearful about repercussions?
AW: This is just a book about my experience. It’s not a whistle-blowing book. I did speak to quite a few people who left our former employers on less than great terms, so in writing the book, I was mindful about what they had signed. It’s pretty common that people leave a company and are paid a certain amount of money to sign a non-disparagement agreement. Basically, anyone who doesn’t have a name is a composite of some sort. That to me seems like a way to make it hard to sift out who said what. There’s plenty that’s not in the book that I wish I could write about, but it isn’t for me to write. Hopefully those stories will come out in due time on their own terms. Everyone I spoke to was supportive and invested in getting it right. Everyone who’s got a name in the book has read their part and given me edits. I hope it’s not an ungenerous book.
ESQ: Something about your book that makes for an interesting reading experience is the lack of names--not just of people, but of companies. What was your thought process behind that anonymity?
AW: I named everyone who’s an actual character who is not an executive. I didn’t do names for companies simply as a stylistic thing. These companies have bad, ugly names. Also, as soon as you see Facebook in a book, you have immediate references for that. These companies are often in the news—not necessarily the ones I worked for, but some of the companies in the ecosystem. It may be rude or irreverent to say this, but I think that a lot of the companies are interchangeable in terms of what I’m writing about, which is culture and power dynamics inside the workplace. My hope is that these are fairly universal experiences.
ESQ: You describe our “blind faith in ambitious, aggressive, arrogant young men” as “a global affliction.” The stories we tell about men in tech are patently uncritical. Men are framed as young disruptors, given a blank check and endless second chances. How do we recover from that cultural affliction and decentralize that narrative?
AW: Third chances, fourth chances. Infinite chances, really. What a good game. A lot of the founder mythology comes from the industry itself, of course, but it also comes from the media. A lot of these people are just normal people, and the more honest among them will say that. The more uncomfortable someone is with being profiled in the Times style section or Wired, probably the better they are to work for. I think the media was very happy to reproduce tech’s narratives about itself for a long time. I think we still have that culture in the industry. What’s astonishing is that the people who are failing spectacularly, whether it’s ethical failure like Travis Kalanick at Uber or business failure like Adam Neumann at WeWork, get more than a second chance. In fact, their lives are blooming. I’m sure that personally, they’re struggling, yet they’re re-absorbed into this ecosystem and celebrated or forgiven.
I don’t have a solution. I think we have an accountability crisis overall, especially in this industry. But it’s a problem everywhere right now in every element of society. Maybe it begins with ratcheting down the marketing of these people.
ESQ: What does the process of accountability look like?
AW: Policy around these issues is fascinating, but unformed. The existing laws around the internet are archaic and inadequate, but a lot of the solutions being floated right now aren’t totally satisfying. Personally, my own interest lies in transparency around data collection. What companies are collecting on people—not just how, but who they’re sharing with. The company that I worked for had other companies using its software. When you’re using an app, you don’t necessarily know if the data is being shared—not just with the company that owns the app, but with any sort of third-party tool. You don’t know where it’s going, whether it’s being sold, or to whom. You don’t know who can see it at these companies, or how long they’re retaining it. That’s a whole sector just begging for regulation.
With something like Facebook or Google, I think anti-trust is a tool. The idea of nationalization is interesting to me—making some of these platforms publicly-owned, though there are lots of issues there. However, I think solving one of these problems will completely demolish the business model. If you solve some of Facebook’s problems, it won’t be a viable business. It isn’t in their interest to address most of their problems, which are tied to this attention economy with engagement as the main currency.
ESQ: Elsewhere in the book, you describe tech as “the scaffolding of everyday life.” What are the drawbacks of being that dependent on tech? What are we risking?
AW: I think that ranges from the practical to the spiritual, if I can be so Californian about it. I wrote that and I believe it, but I wonder if I give these companies too much credit. I just wrote a piece about Amazon a few weeks ago, and in editing, my editor made the point that these companies would like to think of themselves as infrastructure. That made me question my calling them scaffolding, because in a way, they don’t have to be. Calling it scaffolding makes it sound inevitable, and I think that none of this is inevitable. In fact, it’s highly mutable at the moment.
As for practical things, I always find it a little bit alarming that when I’m driving somewhere on a path that the GPS has mapped for me—I don’t actually know where I am. It’s a loss of a sense of place. Obviously there are issues with data collection, surveillance, and control. When my iPhone shuts down, I don’t know how to contact anyone, and it throws my whole day. There’s that dependency where you lose autonomy. Spiritually, it can be atomizing and alienating, this shift where what you value moves from your experience in the world to your experience as mediated by these platforms that have been designed for a common denominator.
I do think that there’s something to be said for boredom and tedium—and work that isn’t toward a goal. Not just work, but engaging with the world in a way where the end game isn’t contributing to the economy. We get into scary territory when our value and our usefulness is completely correlated to our economic output.
ESQ: Does that inevitably lead to a crisis of self?
AW: You have a crisis of self, or you fall for the idea I fell for—that if I was making more money, I was more valuable to society, and therefore better. I think this conflation of economic market value with your moral worth is really dangerous. It’s on the individual level, but on the collective level, too. How do we see people in a society who can’t work? How do we see mothers who decide to stay at home and raise children? You end up in a dangerous place socially.
ESQ: You write, “My job had placed me, a self-identified feminist, in a position of ceaseless professionalized deference to the male ego.” How can the tech industry transform into a place of true respect and equality for women? So often it feels as if the industry papers over misogyny with empowerment conferences. What would actually produce lasting, significant change?
AW: Where to begin? I think that hustle culture can be non-viable for people with families or dependents. The fetish for the person who can work from 7:00 AM until midnight is just not tenable for a lot of women who have kids. I think we need to move away from corporate feminist Lean In narratives. Pay transparency is also near and dear to my heart. I think transparency around compensation, equity, and clear processes for reporting harassment are critical. I don’t think the solution is to put a woman on your board, which seems to be the fix these days. Put a woman on your board, appoint an executive—all good things, but that doesn’t really make the industry better for women. It just nudges the company into thinking of itself as a company that has a woman on its board. It’s about empowerment—actually empowering people inside the company to have a seat at the table, and I don’t mean executive power. I mean the entire employee base.
ESQ: In another part of the book, when you’re given a company-issued fitness tracker, you write that biohacking "isn’t self-knowledge; it’s just meta-data." Do you feel that biohacking is incompatible with true introspection?
AW: Not necessarily. I think that it’s a way of knowing about yourself that works for some people. However, I think of these men in their early twenties who are tracking their metrics and working 12 hour days; I wonder if they really need the affirmation from these numbers that they’re doing well. Maybe it’s actually more about finding a way to feel human in that environment. I think there are other forms of self-knowledge that are valuable, but I don’t think they’re mutually exclusive. For me, I felt like I was generating more data that made my life worse. Once you have a metric, you start working toward it. You start trying to change the number—that’s the whole point of collecting a number. I didn’t want to treat my body like an app.
ESQ: How should tech workplaces change to make employees feel less “like an intelligent artifice,” as you put it in the book, and more human?
AW: These workplaces do try to make people feel more human. A lot of them are very playful—they have healthy snacks and comfy chairs, cute branding, little libraries where employees will bring in books. I feel that you don’t need to be getting your humanity from a company. That’s part of the problem. I feel like people should go into work, do their work, and feel as good as they can knowing that it’s not necessarily their priority in life. I think what’s wrong in tech is this assumption that, if you’re an employee, you should be as committed to the company as the executives—as the people who really have something at stake. Employees have a lot at stake, too, especially at small companies and startups, but if you start getting your humanity from a corporation, then you’re in really choppy water. That’s how you get taken advantage of.
ESQ: Now that you don’t work in tech anymore, do you experience FOMO for the industry?
AW: Absolutely. It’s like I left a cult. It’s not exactly FOMO, because I’ve been so incredibly lucky to be doing what I’m doing now, and I hope I’m able to do it for a while. But I’m also aware that I’ve looped back to a precarious industry. I don’t know if my luck will run out and when, but my feelings of regret are more about that feeling I had when I joined the tech industry, which is that there’s a definite future in tech. If I had stayed, my life would probably be much easier in the long run. I would feel more validated, and I would have more time to spend with my friends, partner, and family.
I miss the camaraderie, and the feeling that you’re building something that might actually matter, that a lot of people will use. That’s intoxicating. Because I work remotely, what I miss is the social element—this feeling of economic momentum. It’s this feeling not so much of being left out, but the question of, “Will everyone leave me behind? Have I made decisions such that the doors of power have closed on me?" In my head, Silicon Valley is like a castle. I was a low-level member of the feudal society, and now I’m very far away from the castle.
ESQ: You write, “Everyone I know is stuck in a feedback loop with themselves. Technology companies stood by ready to become everyone’s library, memory, personality.” For anyone who feels psychologically consumed by Big Tech, what are some small ways they can start pulling back? How can you take back your analog lifestyle without having to become a woodland hermit with no Internet?
AW: Reclaim your own time. Boycotting digital platforms helps you preserve your own mind, but I don’t think that’s the solution. It needs to come from a much higher, individual level. When I’m feeling virtuous, what I try to do is identify what I want from some interaction on the internet. I often find that what I’m actually craving when I’m refreshing Twitter or Instagram is talking to my friends. Picking up the phone or going out in the world really helps. That’s part of what the internet is chipping away at--the materiality of your lived experience. Reclaiming that and re-engaging with that is what I’ve found to be the most valuable solution.
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