Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism
Sarah Wynn-Williams
(Flatiron Books/Macmillan)
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.
***
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.
***
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 it’s portrayed as sexual harassment, but could also be interpreted as a boss, lacking boundaries, suggesting a pregnant underling get some rest. The story is interspersed with what does sound like an inappropriate, exploitative relationship Sandberg formed with a different much-younger woman employee.
There will be more sexual harassment alleged, this of a man (Meta’s Joel Kaplan) culminating in the instances the author speaks out about, leading, in her more-than-plausible account, to her 2017 dismissal from the company. There will be work assignments given during her maternity leave. There will be screwing over the entire country of Myanmar. (In fairness, who amongst us has not done this, truly.)
By Monday afternoon, our fact-checking program in the US will be officially over. That means no new fact checks and no fact checkers. We announced in January we’d be winding down the program & removing penalties. In place of fact checks, the first Community Notes will start…
— Joel Kaplan (@joel_kaplan) April 4, 2025
The main value of Careless People is the presence of quoted text—emails, and spoken—from behind-closed-doors conversations. The reader is being let into private spaces not otherwise available. The writing itself is secondary, and sounds like this:
“I moved to a job at the New Zealand embassy in Washington, D.C., hoping I could get closer to where important decisions about the world were actually made. D.C. seemed like the center of the world. The place where important decisions get made.”
There’s much use of “important decisions” and similar phrasing, but little clarity on what, beyond innate ambition, brought Sarah Wynn-Williams to Facebook. She describes wanting to change the world, to make an impact, to be at the centre of things—motivations that seem blandly positive but non-specific. The language of marketing, or of a college admissions essay, where one says nothing but grandly. She was drawn to Facebook’s revolutionary potential, but what did she want revolutionized? She rightly praises Facebook as a tool for finding loved ones during a natural disaster, but what else about it did she like? Was she dreaming of a better world, or did she want to be a big shot? The between-the-lines answer is, a bit of both.
(More details may be revealed when she testifies later this week at a U.S. Senate Judiciary Subcommittee meeting focused on Facebook’s cooperation with China.)
Wynn-Williams makes the occasional nod to a sense of culpability, but the book’s overall gist is that she was a morally pure soul amidst a sea of baddies. She has many excuses, understandable ones, for why she stayed at the company as long as she did (2011-2017). She needed the health insurance, she was her family’s main breadwinner, and (the maybe less sympathetic) she stood to earn a ton if she stayed at the company and wasn’t fired.
She is ever-ready with background details attesting to how caring she is, how careless everyone is around her. She is attentive to the plight of endangered tuna (Zuckerberg is not bothered), and tries to steer the young founder towards admiring the gentler of the long-past U.S. presidents. There’s some scene where an Israeli security guard appears, and she finds herself trying not to think about where he acquired his skills.
Given the popularity of vice-signalling these days, virtue-signalling has a quaint appeal, but also poses some reliability-of-narrator questions.
She presents herself as somehow outside events that she is participating in. She’s too scrupulous for Facebook, the lone scruple-haver in a sea of (as the cover unsubtly alludes to) sharks. It is only later in the book that she reveals a divide within the company, wherein many outside the inner circle of leadership find the whole endeavour a bit sus.
At face value, one is hearing the tale of a kind, idealistic (the subtitle mentions “lost idealism”) person who was young and innocent and shattered by the knowledge that your colleagues are not your family. She regularly seems not just surprised but appalled each time she relearns that the purpose of Facebook is expanding Facebook, rather than something altruistic. By her persuasive accounts, she pushed back against a lot of corporate malfeasance. The leadership sure sounds blasé at best about Facebook’s role in getting Donald Trump elected in 2016 and in offering user data to China and in monetizing teen girls’ insecurities in creepy ways, and so much more. But the expectations she had of the company, idealism-wise, exceeded what would be reasonable to have if you went to work for an actual charity.
It is now occurring to me that the bad job I had in my 20s is one I had found through a website called Idealist.org. I wasn’t particularly idealistic, but the assumption that this was how recent college grads saw themselves was so ingrained among millennials that this was our job board.
***
Careless People devotes a good amount of space to her status as a cultural and socioeconomic outsider at Facebook. She didn’t know what Louboutin shoes were, and gets a deeply snooty response from a colleague wearing them. Is this bumpkin cred, though, or evidence of a certain disposition? Plenty of women who do not own and could not afford Louboutins know that those are the ones with the red soles, knowledge acquired during an idle flick through a glossy or Sex and the City binge-watch. They may not be the same women who create jobs for themselves at Facebook.
The narrative approach, in which Wynn-Williams is a naif among metaphorical sharks, didn’t have me entirely on board. That a smart, socially adept white woman went law school in New Zealand to a diplomatic job, and then to an American company doing corporate international diplomacy is very possibly less whodathunkit from the outside than if you’re living it. There’s a can you believe they let ME into the room? aspect of the book where it’s like, yes, I can well believe it.
Outsiderness, though, is subjective. As is the whole concept of being self-made. Well into her time at Facebook, the author still presents herself as “a random person from New Zealand.” I had trouble squaring this self-presentation with New Zealand’s prime minister asking after her newscaster sister by first name. Even in a small country, this would not be typical. But I certainly buy that it wasn’t foretold that Sarah Wynn-Williams would work at Facebook, but nor was it that Zuck—the son of a dentist and a psychiatrist—would found such a company.
Marne Levine, the chief business officer at Facebook parent Meta Platforms, is to depart the company this summer @sal19 $meta https://t.co/0nGmx5Z6TH
— Sarah E. Needleman (@saraheneedleman) February 14, 2023
That our narrator is a non-Jew in what she not-inaccurately refers to as Facebook’s “‘largely Jewish leadership team’” comes up, here and there. This is first alluded to when her superior, Marne Levine, does a not-un-Basil-Fawlty-like faux pas of mentioning the Holocaust, and that she herself is Jewish, to a German delegation at Facebook. Wynn-Williams mentions this in the spirit of how awkward and embarrassing this was for her (that is, exclusively for herself), how necessary her own diplomatic skills were, and refers to it later in the book, as the source of negative feelings towards Facebook from Germany. But that’s not the book’s key Jewish moment.
This is it: A fellow Facebook employee tells Wynn-Williams that everyone she works for (he lists them individually) is “‘a Jew who went to Harvard.’” He spells out to her, “‘You’re not like these people. And you’ll never be like them. And the sooner you grasp this, the better.’”
Wynn-Williams describes herself as having been “worried” this man was “drifting into some antisemitic conversation I don’t want to be a part of.” And yet she, not this unnamed man, follows up with the sentence, “Facebook is an elite product, born in an elite college, fronted by elite Harvard grads who show up for other elite Harvard grads who are decision makers in all sorts of places.” She is not insinuating anything about any elders of Zion. The book is most definitely about a sinister cabal intent on world domination, one that simply happens to consist of a lot of Jews.
I don’t love it. But I’m not paranoid enough that I think when someone speaks ill of Mark Zuckerberg, it maligns the entire Jewish People. And it would be a stretch to call this an antisemitic book, given that it is strictly about Facebook-now-Meta and how that company is run. There’s no implication that the vast majority of the world’s Jews, who aren’t tech oligarchs or Harvard alums, have anything to do with it. And Jews are among those who have already published about Facebook’s skeezier aspects.
It’s more that a lot of the book’s ‘colour’—the things that strike Wynn-Williams as noteworthy—consists of her culture shock at spending time with a bunch of Jewish Americans. Someone will phrase things a little bluntly or whatever, in a way that strikes me as pretty normal, but that offends her sensibilities. (I’d be more specific, but fear that in doing so, I would offend Canadian sensibilities, Jewish or otherwise.)
这本书中有一章详细介绍了“奥尔德林”，这是Facebook寻求在中国解禁的项目的代号。据韦恩-威廉姆斯称，该公司提出了各种错综复杂的安排，包括寻找中国合作伙伴、数据收集和审查工具，希望能让执政的中国共产党满意。https://t.co/07PV3ed42G
— 纽约时报中文网 (@nytchinese) March 18, 2025
There is an at least one more Jewish member of Zuckerberg’s inner circle, pictured next to Sheryl Sandberg in the photo accompanying the New York Times review of the book, who goes unmentioned: Meta’s head of product Naomi Gleit, who started at Facebook in 2005. Trivia I know because we were friendly-enough classmates at public magnet high school in New York. Another individual whose trajectory could not have been predicted. The non-zero part of me that picked up this book out of where-is-she-now curiosity about a one-time acquaintance who made it big was either disappointed or, I suppose, relieved.
So who is Sarah Wynn-Williams—a whistleblower, or an unreliable narrator, or some mix? At the end of the day, it doesn’t matter for the book. The point of Careless People became clear when I realized it’s not about her at all. It’s about shedding light on the ethos of the tech sector currently management-consulting the U.S. into ‘efficiency’. And one of the best things about Elon Musk is that, despite being part-Canadian, he is otherwise not one of ours.
Coming soon! The Jewish Angle, a weekly topical conversation podcast hosted by Phoebe Maltz Bovy for The Canadian Jewish News. Click here to learn more and listen to the trailer.
The CJN’s opinion editor Phoebe Maltz Bovy can be reached at [email protected], not to mention @phoebebovy on Bluesky, and @bovymaltz on X. She is also on The CJN’s weekly podcast Bonjour Chai.
