Anna Wiener is a writer and technology correspondent for the New Yorker. Her memoir, Uncanny Valley (Fourth Estate) is the story of what happened when, at the age of twenty-six, she left an assistant job in New York publishing to work in the tech industry: first at an ebook startup in New York, then a data analytics startup in Silicon Valley, San Francisco. It was 2014, the year of new optimism: ‘no hurdles, no limits, no bad ideas’. But for an industry that accepted underdogs and alphas with open arms, she didn’t have to look far to also come across bullies, greed and sexism. From the perspective of a non-technical employee in the industry (someone who worked in customer support, solutions or success—as opposed to engineering or web development), Wiener charts what happens to people when the end goal becomes productivity, not pleasure; when work-life balance is swapped for feeling like every day in the office is summer camp; and when technology stops being a ‘friend’ and instead, reveals itself to be a form of surveillance.
There have been many indictments of the technology industry’s structural inequalities published in recent years—from Susan Fowler’s Whistleblower to Ellen K Pao’s Reset. Wiener’s position is anthropological; one that tries to understand what she and her peers lived and worked through. There’s a level of emotional involvement in the retelling (‘I had compassion for anyone who was trying to figure it out, and there was a part of me that sympathised’, she writes about the young Silicon Valley entrepreneurs she worked for and with). Those looking for neat answers and actionable takeaways about how to fix the industry will be disappointed; however, anyone who has ever looked at the shiny outer casing of Silicon Valley and wondered if it was for them might be able to make up their own mind about what they value and are willing to sacrifice.
Wiener examines the industry as someone who was in search of something better, but began to see that technology valued profit over progress. As we follow her into the Valley, she also questions what makes the industry so seductive in the first place, and what can be considered the last straw for someone to leave behind everything they’ve worked so hard for.
Anna and I spoke about using an outsider status to your advantage, empathy as a buzzword rather than something that’s put into practice, and what it means to move on.
I remember reading somewhere that first-hand experiences of bureaucracy are a bit like recounting dreams: deeply affecting to you, perhaps, but also maybe incredibly boring to the person who is hearing about them.
In the acknowledgements, you thank several former co-workers for speaking to you—with some risk—for this book. How did you navigate balancing your own experiences with what others knew or remembered to be true in the writing of this memoir? Was there ever an urge to hold back anything, or leave out parts of yourself where you didn’t feel like you responded or acted in the way you would’ve liked to?
I like that secondhand recollection of first-hand experiences. Tedium begets tedium. I don’t find first-person experiences of bureaucracy boring, exactly, though they can be incredibly frustrating, or exhausting. Participating in a bureaucratic process is a way of understanding how a system works, its internal logic. There’s value in that.
To your question about memoir: it’s a personal form, and I wanted to be careful to tell my own story, not anyone else’s. I also wanted it to be recognisable to others who were there, in the same rooms I was in, working with the same executives, the same situations. The risk some of my former coworkers took on by speaking with me was legal: many of them had signed extraordinarily restrictive paperwork with our former employers, and so I had to be careful not share anything that could be traced back to an individual. There were a lot of damning, enraging stories that people shared with me, and I did not put them in the book, due to their specificity. They’re not my stories to tell. I do hope someday they make it to the fore.
Memoir is a personal form, and I wanted to be careful to tell my own story, not anyone else’s.
Towards the end of the book, you reflect on knowing you’re ready to leave your job in tech. You said, ‘I had the luxury, if not the courage, to do something about it’. From your point of view now, what’s the difference between having the luxury and the courage when deciding to make a big life change like that?
For me, the luxury was financial, largely. The world is kinder to me than it is to a lot of people: I’m white, I’m a citizen of the country where I want to live, I have a college degree and a large social network. My reluctance to leave tech wasn’t due to my structural position; it was because I was insecure, and scared.
These days, you write about tech culture for the New Yorker. How has distance (or a lack thereof from your earlier life) helped you professionally document the industry as it evolves?
It’s much easier to place things in context, I think—to not have a personal commitment, to examine things from more angles. On the flip side, I am aware that I am now solidly an outsider, and there’s a lot that one can miss from outside of a system. It cuts both ways. I think one way to try to fill that gap is to be rigorous and dedicated, and to speak with as many people as possible who do have firsthand knowledge of a particular institution or system.
You reflect in the book that it was ‘frowned upon’ to see tech as transactional when it could instead be something more noble. What is the joy in seeing work as work (and admitting it’s not always fun)?
I think it can be very useful to see work as a means to an end, a way to support outside interests, relationships, projects. The idea is to engage meaningfully with the world. Some people may do this through work, and that’s great—I feel incredibly lucky to be writing full-time, and take great pleasure in that work. But I find the conflation of personal worth and economic output to be pernicious. Unfortunately, it’s also very American.
In the book, one of your co-workers brings up this idea of ‘sick systems’; the cult-y tendency some workplaces have when co-workers are encouraged to engage in ‘trauma bonding’. When we’re young, certain kinds of workplaces can shape and shift our ideas of what’s considered ‘normal’.
What draws people to these sorts of places, and how can we actively decide it’s not who we want to be anymore?
I think Silicon Valley is particularly good at storytelling: a lot of startups position themselves as world-changing entities, rather than straightforward businesses. It’s not an accident that a lot of employees at these companies are fairly young, ambitious, and have minimal professional experience. The financial prospects draw people to these companies, of course—tech is an industry where people can land high-paying, high-ranking jobs without extensive education or training, and without taking on the debt that tends to accrue from higher education—but there’s an emotional component, too. It feels good to be part of a small club that has a ‘mission,’ especially when the company is doing well, and the world is affirming you financially and socially. The financial rewards are potentially tremendous, life-changing. This is all exacerbated by what some people describe as the ‘cult of the founder’: the obsession that the tech industry has with people who start companies. Silicon Valley’s breathless individualism certainly plays a role.
As for how to decide to leave? I would imagine that’s a little different for everyone. A lot of people burn out, some see that the trade-off isn’t worth it, others become disillusioned or disenchanted by the enterprise. Some simply age out, or grow up. Sometimes it’s not emotional at all; people just move on.
I find the conflation of personal worth and economic output to be pernicious. Unfortunately, it’s also very American.
I was struck by so much of Silicon Valley’s language in the book: ‘down for the cause’, ‘kingmakers’, ‘crushing it’, ‘value prop’, ‘holy grail’. What was your process for noting down, or recording these phrases? Did they ever seep into your own everyday way of speaking at any point while you worked in tech?
Oh, I think they’re permanently lodged in my brain. No documentation required. Corporate garbage language is like plastic. It will almost certainly outlive me.
Clashing with your peers and bosses because you didn’t always speak the same language comes up a lot in the book. One of my favourite lines in one of the chapters reveals how you saw your team when you were leading customer support: ‘I wanted a team of tender hearts. [The CEO] wanted a team of machines’. Do you feel like compassion and empathy are perhaps more valued in the workplace now than when you first witnessed a lack of interest in non-technical skills from leadership because they couldn’t be measured in ROI?
I think people certainly use the word empathy more often. I can’t say that they practice it. Empathy has become something of a buzzword, no? It’s as if, by using it, one has expressed that they have it. I don’t think that soft-skilled labour is any more highly valued than it was seven years ago, though, no.
You recall providing customer support to software developers as ‘like immersion therapy for internalised misogyny’. What kind of a person do you have to be to ‘make it’ in the industry, and how did you deal with knowing whether or not you were capable of becoming this person?
I’m not sure there’s an archetype—it depends on where someone sits in an organisation, how much agency and respect they have internally, what sort of labour they do, their social relationships inside the company. I will say that the industry does seem to be kindest to men, particularly those who are young and white. Personally, I wanted to be ‘down for the cause,’ and I was, at least for a little while. I wanted to fit in. Eventually, my tolerance for it ran up, in part because I began to realise that this wasn’t a system designed for me, that success would require certain compromises I didn’t want to make. I also didn’t want to source my entire identity from the tech industry.
You spent so much time around people who took on a lot of responsibility at a young age, yourself included. Twenty-year-olds were working at companies also run by twenty-year-olds; you noticed that you had the space to make mistakes growing up, while your boss couldn’t. I wonder if being surrounded by entrepreneurialism ever made things look easier than they should’ve been, or if it had the opposite effect: a cautionary tale?
I would never say that running a company, particularly with minimal professional experience, looked easy. Is it easy for certain types of people to raise money to start companies that are exploitative or circumventive rather than socially useful or novel or in the collective interest—one might even ask, is it too easy? Maybe!
There’s a moment in the book where you talk about the ‘performance’ aspect of your job; how everyone’s ‘just reading from someone else’s script’: that the functions you and your peers had were all fairly modern fabrications, from client management to programming.
In a world where we are not often encouraged to think for ourselves (because it could be deferred or automated or suspended in pursuit of something more productive), what advice would you have for someone taking on a job that offers them much more power than they may be ready for?
I try to avoid giving advice, certainly business advice, but my totally unqualified gut instinct is: research thoroughly, move slowly, and seek counsel from people outside of the organisation who have relevant knowledge or expertise. Context and perspective are vital.