Anna Wiener’s Uncanny Valley has one of the best book titles of the season. The title is a term from robotics that hit the mainstream with reviews of the unsettling animated Polar Express in 2004: it refers to an inflection point on the curve of emotional response to things that appear human. Highly abstracted images, like a cartoon, get positive responses, as do authentic humans. Representations that come close to being human but don’t quite make it land in the uncanny valley, and appear repellent.

In this case, the term’s a play on Silicon Valley and its startup culture, where Wiener spent several years working. The implication is that its denizens are almost human…but not quite. The term also, however, applies to the book’s proximity to memoir. It’s literally a memoir insofar as it recounts the author’s lived experiences, but never quite connects the dots between her personal journey and the environment it moves through.

It’s understandable, of course, that Wiener might want to hold herself at a distance even in the pages of her own book, since a recurring motif of her account is the commodification of personal information. One of the author’s tech jobs is at a company that helps other companies analyze their users’ behavior so as to best exploit it for profit. In perhaps the book’s most chilling moment, she reveals just how easy it was not just for those companies to peer into their users’ lives, but for employees of her own third-party company to do so.

“It was assumed,” she writes, “we would only look at our customers’ data sets out of necessity, and only when requested by customers themselves; that we would not, under any circumstances, look up individual profiles of our lovers and family members and coworkers in the databases belonging to dating apps and shopping services and fitness trackers and travel sites.” For an author who came from, and subsequently returned to, the New York writerly world, that kind of experience is bound to give a new meaning to “omniscient third-person.”

The result, though, is an account that feels coolly distanced from both its author and its subject. In a wistful passage, Wiener writes about the peers who declined to follow her remunerative path. “My friends’ world was sensuous, emotional, complex. It was theoretical and expressive. It could, at times, be chaotic. This was not the world that analytics software facilitated. It was a world I wasn’t sure I could still call mine.”

Yet, she remained in her adopted industry for years. She started dating a man who worked in robotics and was contractually forbidden from telling her how he spent his days; and befriended a CEO who interrupted one dinner to casually close a deal that turns him into “one of the world’s youngest billionaires.”

A deal for what company? You can figure it out if you really want to, but one of the book’s conceits is that it virtually never names any of the companies Wiener worked at, interacted with, or even patronized as a mere customer. The reasoning might have been to distance Wiener’s story from the name-dropping, logo-popping environment she describes (and there may have been legal incentives to do so), but the effect is to turn the book into a giant crossword puzzle with clues of varying difficulty.

You can probably name “the home-sharing platform” and “an on-demand ride-sharing startup” and “the search-engine giant” and “the microblogging platform,” and no extra points for identifying “a renowned private university in Palo Alto.” It might be a little more challenging to identify “a gaming company that made a viral farming simulator,” and you may or may not have had recent cause to wake up on a Sunday morning and slug “a viscous liquid jacked up with electrolytes — sold as a remedy for small children with diarrhea.”

Affectations aside, though, Uncanny Valley provides an insider’s view of the decade our utopian online aspirations came crashing down to earth. The book ends with that crash, as the 2016 election makes uncomfortably clear that platforms described as inspiringly transformative or, at worst, purely neutral ultimately facilitated the rise of untethered right-wing populists with the potential to cause almost unfathomable damage to human civilization.

No amount of venture capital can close Pandora’s box now, and Wiener acidly argues that it was always naive to think that it could. The world, she suggests, has fallen prey to the technically dazzling but morally empty machinations of businesses that couldn’t even root toxic masculinity from their own ranks, let alone solve the problems of society more broadly.

It’s a stark vision, and an important observation, but the book remains tough to parse because its author holds herself so persistently at a remove from the world she willingly inhabited for much of the 2010s. The details pile up, but the broader picture remains elusive — which is relevant because Wiener is our proxy in this uncomfortable environment. If we could understand why this world was able to hold her, we could better understand its hold on us.

When she does look inward, she arrives at a bracing insight. “My obsession with the spiritual, sentimental, and political possibilities of the entrepreneurial class,” she writes, “was an ineffectual attempt to alleviate my own guilt about participating in a globally extractive project, but more important, it was a projection: they would become the next power elite.

“I wanted to believe that as generations turned over, those coming into economic and political power would build a different, better, more expansive world, and not just for people like themselves.”

– Jay Gabler