Uncanny Valley by Anna Wiener

Uncanny Valley is Anna Wiener’s memoir of her mid to late 20s working in salt mines of Silicon Valley. At 25, she was an under employed assistant in the declining publishing industry in NYC. She joined a publishing related start up in NY as employee #5, and then got fired 3 months later for “being more interested in learning than doing.” However the CEO sets her up with an interview with a Silicon Valley startup, and a month later she is moving to CA to join the social web revolution as a customer service rep for an unnamed company that is most likely Optimizely.

If you are at all familiar with the tech industry nothing she writes will come as a surprise. 21 year college dropouts with an idea and $10 million in VC money rarely make effective managers. Misogyny is rampant throughout the tech industry. She mentions a conversation with the CEO in which he wants to promote her to get more women in management. Just hiring more women never occurs to him. Stocked fridges at work are not an employee perk, they are a trap to eliminate a reason you have to leave to office. (Do you really think Google serves 3 fantastic meals a day and offers on-site dry cleaning out of the goodness of their billionaire hearts?) Loyalty to the mission (make the founders FU rich) comes before all else.

At one point she is discussing the culture change that is inevitable as a company grows, and she mentions the influx of a professional sales class that is more interested in commission checks than the company mission. I think she meant it as a snide comment, but as one of the professional sales class, I totally get it. Stock options are a lottery ticket. Always take the cash up front. Always. She was about 26 at the time, so it’s not surprising she didn’t get it. I didn’t either when I was working in the late 90s web revolution.

As her time in SV passes she becomes increasingly disenchanted with the chasm between her desire to do meaningful work and the reality that her employer sells digital pickaxes to 21st century data miners. She moves on to another company (Github) that has a better reputation, but the same problems. She had a front row seat for Gamergate at Github, but mostly dismisses it as somebody elses’ problem (SEP). There is a certain level of detached bemusement to her writing. It’s a tone familiar to anybody that reads millennial writing online. What could she do? She was making $100K a year on the lowest rung of the corporate ladder in San Francisco. It’s not like she could afford to quit and do something meaningful with her life.

An interesting stylistic choice she made was that proper nouns are not used in the book. Amazon is “the online superstore” and Facebook is the “social network everybody hates.” It was annoying at first but as I got into the book I realized that it was connected to the resigned helplessness she expresses throughout the book. Facebook is Facebook not because of anything special that Zuck did. SV was always going to create a Fackbook or an Amazon. The name on the sign in front of the corporate HQ is meaningless. Anna is a very good writer and reading time just flies by as her writing has a certain sarcastic blog quality to it that will be familiar to anybody that has been online for awhile. She mocks and laughs, because the other option is to cry at what SV culture is doing to society.

I knew, even as I was moving through them, that I would look back on my late twenties as a period when I was lucky to live in one of the most beautiful cities in the country, unburdened by debt, untethered from a workplace, obligated to zero dependents, in love, freer and healthier and with more potential than ever before and anytime thereafter—and spent almost all of my waking hours with my neck bent at an unnatural angle, staring into a computer. And I knew, even then, that I would regret it.

Wiener has an insightful and funny passage about the moment when “half the programmers I knew between the ages of twenty-two and forty, mostly men, were discovering that their fingers were multipurpose” and finding meaning in woodworking, baking and other offline hobbies. I've written plenty about the need to get offline. Hell, I read this book, in dead tree form, while on Amtrak.

The book is also a front row seat to the growth of surveillance capitalism. As a 25 year old customer service rep she had “God mode” privileges to all of Optimizely’s customer data for every website that used their app. So did all the other 25 year old customer service reps. As the book progresses you can sense her discomfort with it all, but again it’s a SEP, so she tries to ignore it while she makes six figures in what is basically an entry level job. If I have a criticism of the book it’s this. She clearly has empathy for all the hell wrought on the world by her industry, but she seems to be resigned to its inevitableness.

The story does have a happy ending. Github gets bought by Microsoft. As a low level employee she probably didn’t make FU or retire early money from her options. However, she went back to being a full-time writer so I’m pretty sure she did okay.