“There’s a deep sadness to it”: A new book takes on masculinity in Silicon Valley

What happens when you’re not out of central casting?
What happens when you’re not out of central casting?
Image: Reuters/Vasily Fedosenko
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The new memoir Uncanny Valley, by New Yorker contributing writer Anna Wiener, tells the story of what happened when Wiener left a job in publishing to spend five years working in Silicon Valley. Employed first at an analytics startup and then at the open-software company GitHub during the latter half of her 20s, Wiener feels like an outsider in a number of ways. She’s a customer-service worker in a land where engineers reign supreme, a book-lover in a culture where people mostly seem to read for business tips and self-improvement, and a woman in what is still a man’s world.

This outsider quality makes Wiener a sharp-eyed observer of how masculinity norms are evolving in Silicon Valley, shaping tech’s culture and products—and their influence on the world. Sometimes she dabbles in the accoutrements of startup life, mastering the art of coasting on a RipStik caster board at an analytics startup and listening to EDM, “the music of video games and computer effects.” “Was this what it felt like to hurtle through the world in a state of pure confidence,” she wonders as the beat pours through her headphones, “was this what it was like to be a man?”

But Wiener also locates a sadness in the blind confidence that pervades Silicon Valley, showing how faith in data and quantification above all else winds up leaving little space to be in touch with one’s humanity. “Business was a way for men to talk about their feelings,” she observes. “The internet was choked with blindly ambitious and professionally inexperienced men giving each other anecdote-based instruction and bullet-point evidence. 10 essential startup lessons you won’t learn in school. 10 things every successful entrepreneur knows. 5 ways to stay humble.”

Photo of Anna Wiener
Image: Russell Perkins

There’s plenty of sexism to be found in the experiences documented in Uncanny Valley. One colleague makes uncomfortable comments about Wiener’s appearance; another touches her inappropriately. She finds that men respond better to her customer-support emails when she uses a male pseudonym.

But in comparison to the exposés of harassment and discrimination at places like Uber and Google, the overarching portrait of masculinity that emerges in these pages isn’t toxic so much as claustrophobically restrictive, its powers wildly overhyped. Where Wiener first is first drawn to her male colleagues’ confidence in their own superiority, and that of the tech industry, she ultimately concludes, “There was nothing superior about those I was trying to impress. Most were smart and nice and ambitious, but so were a lot of people.” The emperor has no clothes, and tech’s promised revolution is nowhere to be found.

Quartz recently spoke with Wiener to learn more about her thoughts on the men who run Silicon Valley and the culture they’ve wrought. The interview below has been edited lightly for length and clarity.

Quartz: I wondered if you could talk a bit more about how you perceive the tech world’s relationship with feelings and emotions. In Silicon Valley, are they something to avoid? 

Wiener: I do think the emphasis on data and being data-driven is implicitly saying feelings are secondary, if they’re ranked at all in importance. There is an orientation toward quantification.

That’s probably not specific to tech, but I do think it’s amplified by tech. I can’t think of a business culture, except perhaps in the arts, that’s primarily motivated by feelings.

There are, of course, still conversations that happen in business and tech that are driven by emotion. One example I’m thinking of in your book is the scene where the analytics startup CEO calls everyone in after firing Noah, and has everyone take a vow of loyalty to the company. (“If you disagree with my decision to fire him, I’m inviting you to hand in your resignation,” the CEO says.) How do you think emotions getting devalued in work culture winds up impacting the way businesses are run? 

I think it manifests in a lot of different ways. There’s this push for everything to be measurable so you can track progress so you can assign value, whether in equity or compensation or title. I think it is a struggle to quantify a lot of soft-skilled work or qualitative work.

There was an opening for a content strategist at this analytics company. Part of the deal was that this person would be evaluated based on their direct contributions to revenue, so if a blog post led to a conversion. And that is a really specific way of looking at content and marketing. It’s not necessarily looking at it over an extended period of time or as a body of knowledge that accumulates and builds on itself, it’s looking at a very direct monetization pathway. That is a really hard thing to hold someone to, especially when they’re the first person in the job.

I wonder—I don’t know, but I wonder—if people who are not in engineering tend to be held to higher standards because they’re constantly having to justify their existence at a company.

That’s one thing the book illuminates, the way people in non-technical non-engineering positions were sometimes perceived to be second-class citizens. 

Oh yeah. If we could have been rendered obsolete we would have been, no doubt. There’s a real hierarchy there, it’s systemic. And it’s gendered, too; there are more women in non-technical roles. Whether that means they’re actually non-technical is a different topic.

You talk a bit about the body-optimization craze among men in Silicon Valley, the obsession in tech with fitness trackers and tracking your glucose levels. I wondered what your thoughts are on that and things like intermittent fasting, where we see more men in work culture getting in on body optimization. Are the motivations the same for men as they are for women? 

I think there’s a deep sadness to a lot of it. It all tends to be oriented toward productivity of a certain nature—not that it makes you more productive to participate in a community or be available to loved ones, but productive in the workplace.

Some dimension of it has to do with what might otherwise be described as disordered eating. It’s also this idea that because you can track it, you should—that data makes life better, and the quantified life is a superior life in some way.

I resist that on a personal level. There are certain things I would personally like to be better at,  to hold myself accountable to and improve on. I’m not trying to disparage that impulse. But it raises questions about what it means to live meaningfully. What is the endgame of the obsessive metrics on one’s own body, and in service of what project, and for whom?

I think what’s different for Silicon Valley is that it’s more of a self-motivated project. It’s not so much about how you want to appear to others as it’s how you want to be, for yourself—whereas the way women have been socialized is more about seeing your body through the eyes of others, and then trying to conform to a certain pattern. Are women who are working in Silicon Valley participating in these health trends and body-optimization trends in the same way?

It’s a little hard to say. When I was given a Fitbit as an onboarding gift, I was like, Oh, this triggers all of the wrong impulses for me. This does not make me a better worker because it makes me want to eat less. But I know a lot of women who have Fitbits and use step trackers and don’t have the same problems. There’s definitely a difference between having a Fitbit and counting steps and keeping track of blood sugar levels even if you don’t have diabetes.

I don’t want to totally put it down. They’re trying to get the most out of their lives in a certain way. But that phrase, get the most out of your life, it often seems like it’s oriented toward your behavior as an employee.

Yeah, and I think what’s true about business culture and tech culture is there’s an assumption that you should always have a clear goal for every area of your life. And that’s always struck me as odd. 

I think the KPI and objectives and key results, that’s just business culture. We’re being evaluated on a quarterly basis, and let’s get everyone on this timeline. The part of it that’s most interesting to me is the relationship to time, and the tech industry’s general emphasis on speed, acceleration, and rapid growth.

I remember having a meeting with my manager at an analytics startup, he asked me where I wanted to be in five or ten years. I was like, I really don’t know, I just want to be working with interesting people and doing something I care about. He said, I could see you starting a company. He meant this as a compliment. And this was not something I’ve pictured. But this is an industry where the best thing a person can do is start a company and that’s the morally superior pathway. I do feel alienated by that, but I also think I would feel alienated by that ambition toward ownership in any sector.

At the end of your book, you question some of the spiritual and psychological yearning you’ve attributed to the men of Silicon Valley. You write: “I was always looking for the emotional narrative, the psychological explanation, the personal history. Some exculpatory story on which to trade my sympathy.” In fact, you suggest, this was a projection. “The young men of Silicon Valley were doing fine. They loved their industry, loved their work, loved solving problems. They had no qualms. They were builders by nature, or so they believed. They saw markets in everything, and only opportunities. They had inexorable faith in their own ideas and their own potential. They were ecstatic about the future. They had power, wealth, and control. The person with the yearning was me.” Can you say a little more about that, and what that means for the future of tech?

I don’t know that you can be a highly neurotic individual searching for meaning and run a company here. I don’t know if there’s space for that sort of questioning or ambivalence or ambiguity. I think the moment you express uncertainty, the game is over.

It’s clearly a system that rewards certain types of people. I mean that both in terms of personality and in terms of race, class, and gender. That’s not to say these are people who don’t have their own spiritual yearnings, and I’m sure some are motivated by things I project onto them.

But I guess in general, to be successful here, you need to be optimistic, you need to believe in yourself, you need to have a very high level of self-confidence even in the face of absurdity. You need to be able to tell a good story and believe in that story and get other people excited about that story, and, if you don’t have any expertise, wing it. That’s not the sort of person who’s trying to find meaning in everything. That’s the sort of person who’s trying to get a system to work.

You talk in your book about the tendency in Silicon Valley for venture capitalists or people on Hacker News to hold forth on philosophical issues and debates that don’t reflect the actual world we live in, and suggest there may be a moral problem with the way they go about those discussions.

I think this tendency to discuss and attempt to address human issues, social issues, within the framework or logic usually reserved for economic conversations, is morally bankrupt in a lot of ways. I think the intellectual culture here, I have qualms with it because it seems so flattering to power, it’s so vacuous, it’s so ahistorical, and fancies itself apolitical.

A thought experiment is a fun thing. I, too, love to smoke a joint and think, What if the world isn’t the world? But it starts to get frightening to me when it’s people who have the ear and the attention of power and when this pseudo-intellectual mindset is incredibly flattering to power and also presents a way to look at the world where everything is a little bit of a fantasy.