Book Review: 'Uncanny Valley' by Anna Wiener

“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.”

Sometimes, there are just books you read at the right time in your life. Michelle Obama’s memoir, “Becoming,” was one such book for me, as she wrote with candor about the somewhat tumultuous period of change that was her mid-to-late 20s. Anna Wiener’s techno-memoir, “Uncanny Valley,” which chronicles the time she spent working in several Silicon Valley startups, felt like it should have been that book for me but wasn’t.

The premise is simple: Wiener, frustrated and disillusioned in her role as an underpaid and unfulfilled assistant in a major publisher in New York City, leaves her job for the world of tech startups, first for a literary-adjacent e-book startup in the city (Oyster) and then for several other firms in Silicon Valley.

Her subsequent account details her social life and work experiences in San Francisco, first at an always unnamed “data analytics company” and later for another that hosted open-source software projects and had an Octocat mascot — i.e. GitHub. Wiener seems to stumble through her career almost by accident. It's clear she feels simultaneously tethered to her previous mostly analog existence but wants to want to invest, wholeheartedly, in her CEO’s promise that their product will “change the world”; alienated from the Silicon Valley social circle, but also slightly more cultured than everyone around her; ill-at-ease with the gratuitous amount of spending and the wealth gap between those in tech and those on the streets, but unable (or unwilling) to think too deeply and do anything about it. Literary references abound.

Wiener’s writing is engaging, easy to read, and full of delightful anecdotes and turns of phrase that confirm all your worst fears about the tech industry and those who work in it. She details the moods of her volatile CEO, lavish spending on company parties and retreats, copious consumption of alcohol, and countless instances, both intentional and not, of sexism. There’s the male staffer who has his Apple watch set to an animation of bouncing breasts; the female working mother constantly passed over for promotion because she has to take care of her children, her lack of overtime seen as not sufficiently “down for the cause”; gender disparities between the engineering teams and customer service staff. At one point Wiener attends a conference to support women in tech where, at the “Male Allies Plenary Panel,” attendees play bingo with phrases the (male) speakers say, such as “that would never happen in my company” or “mentions his mother.”

“At the center of the board was a square that just said Pipeline,” she writes. “I had heard the pipeline argument, that there simply weren’t enough women and underrepresented minorities in STEM fields to fill open roles. Having been privy to the hiring process, I found it incredibly suspect.”

So why the hesitation to fully endorse the book? At some level, it’s because I never found Wiener particularly empathetic. She acknowledges both personal and social problems, but then never engages with them in any way whatsoever. It makes her accounts of some horrifying situations seem cold and detached, even borderline whiny.  

For example, late in the book she writes about GitHub’s role in the now-notorious “Pizzagate”:

“I couldn’t bring myself to engage. I didn’t know what I was looking at, and didn’t want to. My teammates seemed to have it under control. … I turned my attention to copyright takedowns as they dropped emotions of spinning slices of pizza into our team chat. I didn’t give the repository a second thought until it was all over the news.  

Later, I would wonder if I had missed it because I was more of a product of the tech industry — with its context aversion, and emphasis on speed and scale, its overwhelming myopia — than I wanted to admit. Or maybe it was personal; maybe I wasn’t analytical. Maybe I wasn’t a systems thinker.

Even so: the systems thinkers missed it, too.”

I’m not saying she needed to sugarcoat how she felt at the time, injecting her narrative with false righteousness, but if memoirs aren’t a time to step back and engage in some self-reflection, I don’t know what is. Pushing the blame for her apathy onto “the system” isn’t a solution.

Furthermore, likely NDAs aside, Wiener’s unwillingness to ever give the proper nouns of the companies, even and especially when it was obvious which one she was referring to, was a constant source of frustration. This isn’t bragging by name-dropping at a party: It would have been better for her to just say “Facebook” when she meant “Facebook,” and prevent these firms from having plausible deniability regarding some of the situations she described.

Ultimately there are few lessons and takeaways to be found in her book. The most you can hope for is to finish it and go, “I hope to god I don’t turn out like that if I ever work in tech.”

Uncanny Valley

Anna Wiener

Farrar, Straus & Giroux

2020

Hardcover, 288pp