Life on Autopilot

The concept “uncanny valley” is used to describe an unsettling phenomenon in robotics when a machine resembles a human so much that something feels off. This eerie experience — of seeing something that hits too close to home but not quite — is what ultimately repulses us. That dissonance reflects the hubris of our progress: We’re ambitious enough to manufacture our replacements, and though they might not yet pass the Turing test, they, like us, are soaring too close to the sun.

Anna Wiener’s Silicon Valley memoir is a reflection on its namesake. At the start of the book, Wiener quits her publishing job and moves from New York to San Francisco to start a new life, one more likely to sustain itself in the future. Here, the tech industry thrives as it erodes all signs of San Francisco’s anti-establishment roots and ’60s counterculture nostalgia. In the heart of Silicon Valley, she resets her life at a big data start-up where young CEOs espouse values like being DTC (“down for the cause”), and where extravagance is sustained by unmitigated wealth, power, and breakthroughs. The sell is simple: Together, Wiener and her coworkers can build towards a more purposeful future. But soon the industry’s ethos of optimization falls short: The future is in the hands of a boys’ club, where ambition, like sexism, goes unchecked, surveillance is rampant, and a burgeoning elite not only controls a small fortune but now yields political power. No one is investing in the future they promised or redistributing wealth; they are simply profiting off it. San Francisco is rapidly gentrified, rent-controlled apartments are vacated for people who can pay an entire year’s rent up front, and landmarks are knocked down to make room for cookie-cutter condos. Now the question is no longer whether the future will come but who will get to live long enough to see it. In Uncanny Valley, published in January, Wiener achieves what few memoirists can, which is demonstrating that her personal experiences are not exceptional but rather reflective of a larger system. Her eye for contradictions is unflinching: There’s the CEO of a reading app who misspells Hemingway’s name, or the countless CEOs advocating for customer service on Twitter but compensating their customer-facing employees radically less. Our days of infinite scrolling are far from over, but with this book we get to see where they lead us and who got us there in the first place.

I spoke to Wiener, whom I’ve known on the Internet (of course) for years, about the book and working in a tech-bro universe where your own misery can be somewhat dulled by refreshing your bank balance. While nothing can ultimately fill that void, a start-up’s mission statement, as she explains, can keep you hooked in or “down for the cause” for long enough.

 
Sara Black McCulloch.— At the beginning, and throughout the book, you’re essentially trying to assess your own value, but you’re also seeking out more meaningful work. Can you ever find fulfillment in a job?

Anna Wiener.— Finding fulfillment in work is certainly something that a lot of people do, but I think for me it’s this expectation that work should be a source of fulfillment. A lot of these companies speak of themselves as providing the opportunity of doing “the best work of your life,” or being a place where people can seek and achieve fulfillment. I do think that it exists, mostly when people have autonomy and control over their work, and a choice in the kind of work that they’re doing, but even when that is the case, I don’t think that work is the site of fulfillment in one’s life.

A lot of these companies, do, as you say, draw in people with this lure of vocation and keep them working, almost to the point of burning out. Did making more money justify that to you? Did it change you at all?

To address the first part of your question: I think that many of these start-ups in Silicon Valley will describe themselves as “mission driven.” I think that especially at smaller companies, although certainly this is true of larger corporations as well, a belief in that mission can go a very long way in terms of getting people really engaged with the company, working hard, and committing a lot of time and effort to a corporate agenda.

It was satisfying and gratifying to make more money, to feel that I could support myself, be financially independent, and feel that I could move through my life a bit more easily. I don’t want to overstate any hardship, because I had a comfortable amount of privilege. I felt secure. For me, it was a feeling of independence more than any sort of insecurity. It was the mission — the feeling of being in a group, of having momentum, of working towards something with other people I respected and whose company I enjoyed — that was the most seductive to me. It was this feeling that what we were doing was going somewhere and that I could individually contribute. It was the feeling of being useful, which is how I’ve come to describe it.

You were in a customer-facing role, and I want to know your stance on undervalued jobs like customer support, retail, account management, sales, and even recruiting. Soft skills are crucial to these jobs; there is a rapport you need to maintain with customers for their loyalty, and while it’s something these companies need, they don’t necessarily value them the same ways as the more technical roles.

I have a lot to say about that.

You touched on this so well in the book, because these roles aren’t compensated well, but they’re essential to building customer loyalty, especially for retail-driven tech companies. And yet, we’re still debating whether the minimum wage should be raised, and we still don’t respect people in these roles. You even had to start presenting as a man online so that people would treat you with a bit more respect. I wanted you to unpack this a bit more.

The comparison to retail is interesting and valid. Employees with soft skills — which often translate into communication skills, whether that’s customer support, account management, sales, marketing, or recruiting — are often coded as feminine. They are undervalued and tend to be underpaid. I always found this difficult to square, because customer support, especially for a start-up, is essential. When you’re working on a technical product that requires a certain amount of hand-holding for people who don’t understand it, [customer service] is the face of the company. We had a CEO who would sometimes tweet about how customer support was the secret weapon for any start-up, and I always thought this was funny, because the people on customer support were among the lowest-paid people of the company. And we were all making full-time salaries, very livable salaries (relatively normal for the industry for full-time employees), but it still didn’t compare to the engineering salaries.

Part of that is the belief that soft skills are easy but also that there is a larger employee pool [to choose from], although having been in the position of trying to hire people for customer support or for content-marketing jobs, I found that it was quite difficult to find people who do have communication skills and who can especially be excited and curious about the technical stuff. The prized skill set in the industry is an engineering skill set, and it’s considered hard skills. I think that’s a false dichotomy, because some of the best engineers are those who can also communicate their ideas to other people, and so you would ideally have someone with a mix of characteristics or talents. But because engineering and software are so central to the business, there is also this mindset that human interaction is inefficient, and that if you can automate a process then you should.

How did you keep track of all these conversations and scenes? There is an incredible amount of detail, and I wanted to know if you were intentionally keeping track of everything so you could write about it.

I didn’t intend to write about it, but I did have a lot of inadvertent documentation. Some of these scenes I just remembered very clearly because when they happened, they just rattled me. I have a memory for highly specific detail because it’s where my mind goes when I’m in a situation that’s destabilizing. I also have long emails to friends about my life and what I was thinking about, what I was dealing with at work, and different relationships I was having with people that were stressful and exciting, so that correspondence was the closest thing I had to a diary. Then there were text messages, photographs, blog posts, and corporate material that was public and that I could access. I also had this particular document that I had written up like a self-assessment for my annual review and didn’t submit it in its entirety because I laid out all the different sets of things I had encountered and got the feedback that it wouldn’t be advantageous for me to make those complaints without any formal reporting structure at the company. I have that record and records of conversations with coworkers over text message about stuff that was happening at the office. This didn’t happen that long ago, and I have a pretty good recall for a lot of it. I also interviewed former coworkers and talked to friends that I knew at that time just to place myself in their memory, and for a gut check as well.

There is a lot of digital material, and it’s funny, I’m only realizing this week after talking to people about it, that a lot of what I find creepy about the way we accumulate and store digital content has actually been very helpful to me as a writer.

Speaking to that and given how easy it is to go back into someone’s history and read through it, how did this affect your own browsing patterns and your relationship to surveillance?

Working at this analytics start-up helped me understand the business model for a lot of other companies and made me much more aware of what kind of information is being collected and to what ends, and it’s made me wary of most services. I definitely don’t have a robust digital ecosystem of apps that I’m using all the time. I try to streamline it. I also have no interest in contributing a ton of personal content, which I realize is funny because I’ve just written a memoir and that will be dispersed across the Internet and also some other ways. I’m also not a big photo poster. It has been really unsettling to see photos of my own face online, because for so long, I think I did a good job of keeping it off the Internet.

Uncanny Valley started out as an essay for n+1, after you had taken a break from writing. What did it feel like returning to it, and finding your voice while you were synthesizing your experience?

It’s funny, because my first job in San Francisco involved some copywriting. I was writing a lot of emails to customers explaining this software product, and so I feel like I lost any kind of writing voice. It became a corporate writing voice, and I always found it very hard to do both at the same time. I had this idea that I would write these short stories or a novel in San Francisco. I didn’t. I just wrote emails. When I started writing for n+1, and when I picked writing back up in 2017, I found [my experience in Silicon Valley] quite exciting to write about. I had spent so long trying to section off that part of my life and not treat it with the same literary interest as I would treat any other part of my life. I always separate work and creative . . . I don’t know what I would call it . . . creative writing?

I wrote the book with my friends in mind. I wanted to tell jokes that my friends would find funny. I wanted to disguise things in a way that would be clear and engaging to them. I took great pleasure in writing about this world in that way — in a sort of observational, descriptive but not solutions-oriented, not polemical way. Just a personal way, because it’s a world that resists observation and emotion. It was one that I found so emotional and rich. I felt that I had found something that was incredibly interesting to me and pleasurable to explore as a literary subject.

Did that give you more perspective on what was going on?

It definitely helped me to understand that what was happening to me wasn’t exceptional, that my personal experience was more reflective of a system. My hope is that my personal narrative illuminates the structural narrative. This is happening in reverse, where I’m starting to understand the incentives of the industry and what I was running up against as something more systemic and common than it had felt. I started doing that in reverse, where that helped illuminate my own experience and contextualize what was going on.

When you did decide to quit your job and move on, you were conflicted and said that you still felt “safer inside the machine.” Can you explain that moment?

I felt that my life working in the tech industry felt very stable and could be stable, and if I could do what was asked of me and trade my time for money then I would be taken care of, in terms of health insurance and having a robust workplace. I don’t know, I felt like I could put my life on autopilot and that would be safer — especially at a time of political turmoil, that felt amplified for me. In hindsight, I think that I was anxious about everything at that moment in my own life and outside of it. I was scared to make a change. I was scared not just to be outside of this powerful industry that seems to be growing in power but also to be critical of it. It’s just about power and feeling safer when you have proximity to power or you are protected by power because what you’re doing is flattering to that power or supportive of it in some way — that to me just felt safer. I felt like I was on the winning team, even though I didn’t want to be there anymore. I had to grapple with that feeling of, “Do I trust myself enough or trust that I will figure it out enough to let this go?”

Has anything been coming up during interviews that you didn’t originally consider? Or has this conversation been tied to other industries?

People seem to really be engaging with the ideas and the book. I do think that some wanted a more explicit argument or polemical approach or a condemnation on more explicit terms, which I understand. It’s been interesting to get that feedback, and I take it to heart. In terms of other industries, there are some parallels to higher education and with people organizing and trying to negotiate the incentives of private universities. Obviously, people are interested in the comparison between Wall Street and Silicon Valley: Is this the new Wall Street, and what does this look like? Why are people so critical of Silicon Valley and not Wall Street? I would say people have always been critical of Wall Street. There is a lot of important reporting that is done on Wall Street, on banks. I think that the base difference is a narrative difference, where Silicon Valley has sold stories about itself for decades that are not lining up with its actual impact on the world, and something like Wall Street has never lied about its motivations or its ambitions or mission statement. That’s the comparison that comes up most commonly.

When it comes to myths and origin stories, I think about Steve Jobs and how he built or changed his own narrative over decades. It took a lot more time for him to solidify it, compared to Mark Zuckerberg, who had a feature film made of his life six years after he founded Facebook. A narrative like this for a business, person, or ideology develops so much faster than that of Jobs or even Bill Gates. Does the Internet now help with proliferating that, or is this just what we expect of tech and business savvy?

The companies who have had these grand narratives for themselves are Internet companies rather than Apple, which is more of a hardware company, or Microsoft, which is software but not a social network.

It’s just that some stories gain momentum faster than others.

Yeah, it’s interesting that the companies with the strongest mythologies around them, self-perpetuated mythologies, are companies like Google and Facebook, which are ad networks. Advertising is storytelling: It’s all about convincing someone of a narrative. In a way, I think that the strength, proliferation, and acceleration of those corporate narratives reflects the products themselves. Everything in Silicon Valley is this steroidal capitalism, and I think that what you’re seeing, narrativewise, is a reflection of what’s happening in the business model as well as the product priorities, if that makes sense.

It feels like it’s very hard to counter these narratives too. There is amplified growth, but no regulation of it, and there are consequences regardless of their intent: These have impacted elections and people’s lives. There is a sense of detachment too.

The culture is shifting in some way so that with software, infrastructure dictates the form — and so that can mean the way people communicate on platforms where the digital-visual template is consistent and homogenous, or it can mean that the way they interact is dictated by the incentives of the business model, which are optimizing for engagement and for constant reengagement and reward very specific types of content. It’s a self-perpetuating cycle. There will be no real reckoning with what tech has done to the culture until there’s a reckoning with the business model.

Did you intentionally leave the names of these companies and platforms out? Was this a strategy so that the reader wasn’t distracted by these brands and our own interactions with them?

I didn’t want the companies to be distracting and aesthetically unappealing, but I also wanted to gesture towards the interchangeability of a lot of them, especially when I’m writing about internal culture. I don’t think that what I experienced at these companies was so unique. It was the function of a culture that rewards things like speed, acceleration, scale, youth and potentially even lack of expertise, that puts a certain type of young man on a pedestal and injects a ton of venture capital into a growing start-up with the expectation that it will grow very quickly. I wanted to point out that this isn’t just one story of one company, that it’s reflective of a greater value system that should be called into question even more than any other particular start-up or organization.