Uncanny Valley by Anna Wiener


Anna Wiener transitioned from a career in publishing in New York to a working in various non-technical roles at startups in Silicon Valley, including Github (although she doesn’t refer to any by name). Her memoir talks about her experience working in tech, drawing on perspectives from her identities and experiences as a woman, a millennial, and an outsider to the industry.


As a woman with a career in tech I can vouch that much of this book rings true to many of my experiences. I’ve never worked in Silicon Valley or at a startup that’s blown up to the degree that the startups often did during the time Anna Wiener was working in tech, but I have been a software engineer for the past 3 years. Like Wiener, my background was in literature (and linguistics). I had to drop my academic interests when I couldn’t get a relevant job, so I went to a coding bootcamp in NYC and got a job in software engineering immediately after. I quit my first two tech jobs in large part because of sexist attitudes among management. I’m currently on my third tech job in as many years, coming up on a one-year anniversary in March. It’s been good so far. Not many tech companies are. Cross your fingers for me that it stays good.

A lot of what Wiener covers in her memoir relates to sexism, but a lot of it also relates what it’s like to be a “non-technical” worker in a highly technical field. I haven’t seen that side of the industry directly, but I’ve gotten small tastes of it by having a nontraditional background (humanities instead of computer science) and by hearing about the experiences of friends who work at tech companies in non-technical roles. That is to say that the distinction between technical and non-technical workers at tech companies is often fuel for another form of elitism. 

Uncanny Valley was the first non-YA-fantasy book I read in this past year of reading, so it’s been a while. I don’t remember many specific scenes or passages from it, but I think that might be less because of how long it’s been and more because at a certain point it’s hard to dedicate more space in my brain to remembering misogynist things tech bros have said than what’s already been taken up by my own experiences.

Trying to recall my overall takeaways, I can think of a couple of main points. The first is that the author is unrelentingly hard on anyone who buys into any of the promises of the tech industry, including herself. The tech industry is by and large problematic as hell and almost certainly is actively making the world a worse place overall, but it doesn’t present itself that way. It presents itself–in nearly each and every company, be it brand-new startup or long-lived powerhouse–as a way to change the world. And I think a lot of people who work in tech legitimately believe that their ecommerce app or b2b software or artisanal hipster beverage service is changing the world for the better. I don’t know if most of the people who think this way are just totally un-self-aware, or unobservant, or intentionally delusional as a defense mechanism against bleak reality. But a lot of people in tech legitimately think it’s a positive force in the world. I can’t blame people for wanting to believe that. If there’s a lucrative career right in front of you, wouldn’t you want to believe that it wasn’t going to contribute to further ruining the climate or enabling the surveillance state or preying on a depressed generation’s overworked dopamine receptors? Especially given that for some people, tech has become a powerful tool for socioeconomic mobility in an era of very few such tools. I don’t blame people for wanting to believe in the promises of tech any more than I blame people for believing in religion. Both are a way to find delusional comfort against an uncomfortable reality. It is admirable that Wiener was able to climb out of the trap she and so many others have fallen into, but I don’t think she needs to be as hard on herself for falling in the first place. 

The other takeaway I can remember is a little more straightforward. It is a very observational book. For all of the eloquent ways Wiener enumerates the problems with the tech industry, she has little to say in the way of better paths forward. There’s a passage about unionization in one of the chapters, but that’s about it.

That said, her observations were validating for me, having had similar experiences. If you don’t work in tech and want to know what it’s like, this is a good book for you to read. Same as if you do work in tech but you’re a man. I think the book is worth reading for many reasons.

The only thing that really annoyed me about the book was her steadfast refusal to use company names even though she’d drop enough hints that it was obvious. There are reference indexes you can look up when you read, though.

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