Facebook's inside story is a disgustingly good page-turner
A review of "Careless People" by Sarah Wynn-Williams
Sarah Wynn-Williams is at a meeting with her colleagues at Facebook in January 2014 when her water breaks. She is rushed to the hospital for the delivery of her first child and her feet are in the stirrups, when a text message interrupts her contractions. Her boss Sheryl Sandberg wants her to send talking points for an upcoming meeting. Fighting against her husband and her doctor, Sarah opens her laptop, types out an email, hits send, and only then does she get back to delivering her child.
Sarah Wynn-Williams, born in New Zealand, surviving a shark attack as a teenager, working as a policy lawyer and a UN diplomat is obsessed with Facebook. She creates and pitches a job that doesn’t even exist, and when the top brass at Facebook see themselves as a tech company, she imagines it as the global superpower it could become some day. She flies across the world introducing world leaders to Mark Zuckerberg who comes to see her as a friend and writes her thank-you notes. Even while delivering her first child, Sarah is thinking about her child (That child’s therapist is going to make bank some day).
And then, 11 years later, Sarah gives this statement at a hearing chaired by Senator Josh Hawley:
My name is Sarah Wynn–Williams and I served as the director of global public policy at Facebook, now Meta, for nearly seven years starting in 2011. Throughout those seven years I saw Meta executives repeatedly undermine US national security and betray American values. They did these things in secret to win favor with Beijing and build an$18 billion business in China.
After working at Facebook for seven years, Sarah throws Facebook under the bus, writing a memoir that portrays Facebook as an amoral machine run by careless people who only care about power and profits. Facebook retaliates by placing a gag order on her and threatening to make her pay $50,000 for each time she mentions Facebook in a “disparaging manner”. Despite all their attempts to suppress her from speaking, her book becomes a bestseller.
How Sarah went from Facebook’s darling to Facebook-enemy-number-one is what the book Careless People is about.
Facebook wanted profit, not power, but it got both
Meta – which now owns Facebook, Instagram, Whatsapp, and a bunch of other companies – is one of the most powerful companies in the world, and even in the history of the world. If you’re young, you probably don’t remember a time when it was an exciting novelty that let you reconnect with old friends or chat up dates.
Sarah came from that world but she sensed where Facebook could go. She didn’t see it as a tech company restricted to America. Facebook proposed a mission of “connecting the people of the world” and Sarah trusted that they actually meant it. But even Sarah’s first meeting with Facebook shows a crack that lies at the root of this book – Sarah is interested in Facebook’s potential as a global force for good while Facebook’s leaders are interested in its ability to make money. To her credit, she isn’t naive. Sarah suggests that by appointing her as a director of global policy, Facebook will have an easier time expanding to other countries. The only reason she gets the job is by appealing to their profit-making motive, but she believes that once she’s inside, she’ll get to influence Facebook’s direction.
That seems like an honorable motive but it’s also the hardest thing to buy about the book. Sarah is shocked that these out-of-touch billionaires aren’t as relatable as she imagines them to be, and their duplicity bothers her. What we get in the bargain is juicy gossip and an inside view about how deals are done in the backrooms.
There’s a scene in the middle of the book where Sheryl Sandberg, the COO, is meeting the Irish Prime Minister at a time when the European Union is tightening its restrictions on tech companies, and they want some country to be a privacy watchdog. Facebook is at the highest risk, and Ireland is at risk if Facebook leaves because Facebook makes Ireland rich by using Irish shell-companies to avoid taxes. So they both need to do something about it. The Irish Prime Minister suggests something like this: “Pretend to the media like we are giving you a hard time about privacy and audits. If the European Union thinks we’re strict, they’ll give us the job of supervising you. Once we get the job, we’ll let you do whatever you like.” The two shake hands on it and don’t write it down.
But Sarah is in the room where it happens. There’s so much in the book that I can’t cover here or don’t want to cover because she tells the story so much better!
This fly-on-the-wall vantage point is what gives Sarah insight into underhand dealings in the upper echelons of the world. From Xi Jinping to Barack Obama, from riots in Indonesia to dealing with the junta in Myanmar, Sarah is Facebook’s touchpoint for dealing with political power. She writes in the prophetic tense of predicting that something would go South even as she’s in the middle of it, giving every encounter an ominous feeling: “I was happy about my deal in Myanmar, little did I know that…”
And when things begin to collapse, it isn’t that surprising. You’ve seen Facebook being smeared in the news for inciting riots or selling data to enemy countries or influencing Presidential elections. Facebook sees it all coming and chooses to do the wrong thing at every juncture. Mark Zuckerberg goes from being coder to CEO to celebrity to kingmaker, and he even imagines himself as President, restructuring the company so that he can take a break if he wants to campaign. World leaders want to take selfies with him and curry favor when they know that Facebook is an important tool to winning elections.
But since Sarah shares every dorkish detail about him, he looks like a petulant wannabe. I wonder whether Mark Zuckerberg can ever trust anyone again. Does he stay up at night wondering which employee is planning to betray him next? Does he imagine people laughing at him behind his back? Or is he going through their Whatsapp chats and planning the next move? All he wanted was to be liked, smh.
People on the inside, people on the outside
A running theme in the book is the difference between what people say and what they do. What they claim to stand for vs the decisions they take under pressure.
Sheryl Sandberg, the COO, is a high-performing leader and a champion of women’s rights in the workplace on the outside. But in private, she chews up her hairstylist, yells at subordinates, and suggests things that are borderline sexual harassment. She uses company resources to promote her book and treats Directors like her personal assistants. Yet nobody turns against her because they know that keeping her happy gets them personal favors.
Mark Zuckerberg is a different beast. You’ve seen Jesse Eisenberg play him in The Social Network, you’ve seen him become a meme, a podcast guest, and a social villain.1 This book’s version of Mark oscillates between ruthless sociopath and autistic goofball. From Sarah’s assessment, Mark is an unrelatable nerd who is desperate to be liked. He sings karaoke, plays Catan, reveres tyrannical Roman Emperors and wants to eat authentic bluefish Tuna while flying in private jets, renting out mansions, and living in prefabricated bubble houses when they travel abroad. He wants to dominate meetings with political leaders, but he can’t even wake up before noon for a meeting with the Colombian President.2
However, this insistence to make Mark look bad is one of the weak points of the book. Think about it – when I pick up a book named “Careless People”, I’m already expecting to be shocked, disgusted, and repelled by the people at the center of the book. Sarah plays into that schadenfreude by twisting every innocent thing that Mark does into something awkward, unrelatable, or heartless. Why is it wrong for a CEO to want to eat tuna or sing karaoke? She’s so obsessed with what Facebook could have been and why it isn’t going according to her vision that she doesn’t do enough credit to the fact that it’s incredible that something like Facebook does exist in the first place. That Mark built a technological empire and that he’s still growing it actively gets no mention. The trashing actually made me sympathize with the guy a little.
But there’s no denying that these people at the top are a little bit… mental.
For example, when they’re planning to go to South Korea, they all have arrest warrants in their name because they broke the Korean government’s laws. But they think the government is bluffing. How can they test the waters before landing in Korea? They decide to send a junior ahead to see if the government really has the guts to arrest someone. This scapegoat isn’t even addressed as a person. They just refer to them as “a body” for arrest. Luckily, he isn’t arrested.
But here’s the crazy thing – when this strategy works out, they even institutionalize it. In India, the Facebook office is being raided by the police so often that they appoint an ex-police captain to handle “arrest situations.” His job is to just get arrested and go to jail when there is a problem.
This dehumanization is a persistent theme in the book. When Sarah has a baby, she is expected to do the job of mothering invisibly without mentioning it at the office. When a contractor has an epileptic fit and is bleeding on the floor, the colleagues around her don’t even notice, saying “she’s not part of Facebook.” When China asks Facebook to hand over data and ban problematic people, Facebook’s concern isn’t about censorship – they happily comply with China – but about what it will say at the senate hearings. They practice mock questions, write answers, edit the answers because they reveal too much, and figure out how to lie just enough without getting caught.
By the time I’m following Facebook’s targeted advertising to teenage girls with body image issues, or how an unwillingness to translate Facebook’s website into Burmese is causing a genocide of hundreds of thousands of people in Myanmar, I’m already sick to my stomach. For all her flaws with moralizing, Sarah is an incredible storyteller who puts you right in the middle of a scene, whether it’s a crisis control situation during a riot or a board meeting in Silicon Valley or an ICU where she’s bleeding out. The only humanity in this dehumanized environment flows through her.
Weaponizing memoirs
So here’s my problem with this book. I really, really enjoyed reading it.
Yet, at every turn, I knew that Sarah wasn’t saying the complete truth. She was saying just enough to shock me into disgust for the overlords of Facebook and trying very hard to portray herself as a saint.
It’s not hard to empathize with Sarah. She’s one of the few people who cared about Facebook retaining its moral core, as even her documented emails and letters show, and she’s a survivor and an outsider who fought her way through all of this by literally creating a job that didn’t exist and then making it one of the most important parts of Facebook. She somehow met a hectic schedule while dealing with pregnancy and motherhood and sexual harassment and sexism (five separate issues, all of which I’m unlikely to ever deal with. So good to be privileged).
Yet, the problems are as much with what she doesn’t reveal as what she does. All of Facebook’s leadership is up on display. Every decision of theirs that went wrong is scrutinized and dissected by Sarah, with her commentary on what should have been done differently. Yet I don’t know about a single major decision that Sarah herself took and messed up. There’s no real vulnerability here because she’s scared of the hit the story will take if her character is called into question.
A story needs a vulnerable protagonist to succeed (this book is a story after all, even if it really happened), and she inserts “mistakes” to build that persona. But her mistakes are always of the foible variety – she types an email in the delivery room (“Am I a bad mother?”), she mistakenly stays in the wrong hotel and arrives late for a meeting (“I’m such a klutz”), she takes responsibility for a public event gone wrong (“I botched such a huge event”), and lectures Mark about strategy (“I’m so stupid that I gave advice to my boss”). But none of these was a conflict of values that went against what she stood for. She never falters in her agenda for a moment… and that’s a little hard to believe?
I’m a reasonably calm guy. Yet there are times where I’ve had meltdowns and done stupid things that hurt people. Those are the things I wanted to see from Sarah’s life.
There’s also the question of the timing of the book and the manner she left Facebook. Sarah realizes this herself. She knows that as the reader is flipping the pages, they’re also wondering, “If she knew Facebook was this bad, why didn’t she just leave?” Sarah brings this up herself whenever she faces a dilemma. The first time she thinks of leaving Facebook, she’s pregnant and needs stability. I can understand that. Then the baby is born, and two years pass. Nothing has changed and Facebook is still the same morally depraved company it was (why not leave?). The next time she feels like leaving, she says “I messed up something in my Visa application procedure. Now I’m reliant on Facebook and can’t leave.” (At this point, I’m like “Okay…?”) And before I know it, Sarah is stuck with workplace toxicity again and her reason for not leaving is “I was pregnant. Again.”
Finally, she doesn’t resign from Facebook. She’s fired.
It’s her life. She gets to choose or leave from a toxic workplace. But if I had to empathize with her reasons to not leave Facebook, it was hard to ignore that she did have a choice on many occasions and chose not to take it for whatever reason – stability, a need to maintain a standard of living, health. Since she’s making her moral superiority the basis of criticizing everyone else at Facebook, maybe she felt compelled to justify not leaving. But here’s the thing, if she had said, “Hey, I know I could have left Facebook at any point, and I chose not to because I valued my stability more than doing the right thing,” that might have worked better for me. Having to judge “who was right” at every point took me away from the more important point – that we live in a world where companies are entitled to demand the most absurd things from us and that there are employees who will choose to satisfy these demands in a circus of sycophancy. It’s the system that is broken.
I thought I was reading too much into it until I saw the Senate Hearing I mentioned at the top. Sarah truthfully repeats everything about Facebook’s collusion with China in the hearing and its targeted advertising to teenage girls. But a huge part of her book was criticizing Facebook for getting Donald Trump elected into office and what a bad result he was for the world. She conveniently omits even a passing mention of him to the Republican senator who is questioning her with his own agenda. She conceals some things to have the opportunity for other things to be heard, and I wonder if she did that with the book.
Does this take away from the point that this is a wild ride of a book? No.
It’s an incredible story and I admire her courage for speaking against one of the most powerful and ruthless entities on the planet. I’m not sure I could do anything remotely close and I highly recommend reading it. But if you do read the book, I’d suggest you read and watch the other side’s take too. Reading the book won’t change anything. Facebook will continue to sell our attention to the highest bidder and when I’m done writing this article, I will have the hard decision of choosing between Instagram or Whatsapp when I open my phone. But at least I know how exactly I’m being screwed over, and that gives me some satisfaction.
Jesse is playing him again in the movie version of Careless People which he is also directing. I’m betting this line from the book will make it to the film and I really hope Emma Stone is the one saying it as Sheryl Sandberg: “What do people do after quitting Facebook or Google? Exotic travel for a year or more before becoming bored of that, then transitioning to getting very fit or some other personal goal. After achieving that goal, buying a boat or some other extravagant hobby purchase, and then finally getting divorced or going through some other personal crisis. If they come back from that, maybe they attempt their own start-up or fund, or most likely, philanthropy.”
Mark is unintentionally hilarious at times. When they’re practicing handshakes and gestures to meet the Korean government, Mark is throwing up gang signs and fist bumps trying to look hip. It reminded me of this Ryan Long video showing Zuck in 2020 vs 2024.