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A bad job: Facebook’s ‘Careless People’ meet their match in a new tell-all book

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08.04.2025

It is not of memoir-worthy earth-shatteringness to have had a crummy job. Even those of us who’ve been lucky professionally had duds along the way. A boss from my early 20s berated the office for misdeeds entirely in her head, all part of the place her underlings held in some psychodrama. The more creative will use these experiences as inspiration for fiction. The less-so will content themselves with ranting to their friends. That is, unless the bad job happened to be somewhere that is itself newsworthy and glamourous. A company that everyone’s existence is somehow a product of. That’s where memoirs enter into it.

Careless People is a tell-all about a place where a dream job turned out to be a nightmare: Facebook. More on that soon enough, but there is a publishing subfield in which this book exists, and that needs explaining.

Despite having no public profile before her book emerged in March without advance notice, Sarah Wynn-Williams manages to be of a piece with other 2020s memoirs—think Prince Harry’s Spare or My Body by Emily Ratajkowski—that depict hyper-glamorous scenes, but implicitly admonish the reader for thinking anything enviable is happening.

On some level, the authors have to know their books exist because they depict rarefied worlds everyone wants to glimpse behind the scenes. But these glimpses are not presented in the spirit of mindless escapism. There’s much name-dropping in Careless People (within the span of a few pages we get a list that includes Beyoncé, Leonardo DiCaprio, Big Bird, Malala, and the Pope), but all in the service of pointing out how rotten it is at the top. (Some Canadians, too—early on, Facebook founder Mark Zuckerberg is snubbed by then-Prime Minister Stephen Harper.) You might wonder what it’s like at Davos, but Wynn-Williams would have you know it kinda sucks.

The book is also, in some ways, a real-life counterpart to Leigh Stein’s hilarious 2020 novel Self Care. It’s about start-up-culture hypocrisy, the way companies that talk a good game about how they’re saving the world are quite possibly doing something else.

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This memoir begins in earnest with the time Wynn-Williams survived a shark attack as a child. It’s the sort of story where, if you have it in your repertoire, you’d be a fool not to tell it. It’s horrifying and gruesome and it involves a shark. Her parents didn’t take her seriously when her health failed during the recovery—and she almost died.

As I was reading this part, I found myself wondering how interesting anything involving tech bros and bro-ettes would be, with that act to follow. Careless People has been touted as the new release Mark Zuckerberg doesn’t want you to read. More than touted: Meta, now the parent company of Facebook, has taken legal action to prevent the author from promoting it. Yet much of the book consists of the author seeming stunned to learn things that would not have startled outside observers at the time. The Social Network came out in 2010, the year before Wynn-Williams started at Facebook. Zuck comes across as a dweeb, Sheryl Sandberg (former Meta COO and Lean In author, now vocal Israeli hostage-freeing campaigner) as a ruthless girlboss. The reveals include the fact that the reason Facebook has so many workplace amenities is that they want you to have no life outside of work, which is one of those things you would have surmised even if you yourself have had zilch to do with that sector. I’m reading, finding everything about as I’d pictured it, and wondering when the other shoe will drop.

Then a whole DSW’s worth of shoes start dropping.

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On a private jet, Sandberg insists a heavily pregnant Wynn-Williams join her in bed. It will shock you to know that I was not on this jet and am going by what’s in the book. It’s a strange scene because........

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