Careless People is a very enjoyable book, and, depending on who you talk to (and presumably based on how much Meta stock they still own), people with knowledge of the events in the book either strongly agree with author Sarah Wynn-Williams or they say she’s full of shit. But in the course of her scathing assessment of building one of the most dangerous and powerful political tools in history, she also did something magical: She made me like Sheryl Sandberg.
As a woman, I know it is offensive to say I never much cared for Sheryl Sandberg, the former COO of Meta and the person everyone agrees made the company a monstrous success. I was there in the early 2010s when “I went to a live reading of Lean In” was a bragging right amongst professional women who were all eager to prove that they too had the stuff to build something ambitious while never fully joining the boy’s club. Like a vision out of 1980s Hollywood, Sandberg was a working woman, decked out in stylish power suits, with a platoon of assistants and a loving family, too, and she sold this promise to a lot of other women with much smaller paychecks and far fewer assistants.
I always thought Sandberg’s bit was too much. Her victory lap as a supreme Girl Boss felt baldly like a tool to market her book instead of a philosophy she lived by. She seemed to project an image where every flaw was carefully chosen to further the story of womanhood she was selling. It felt like just another iteration on the deeply annoying and offensive adage “a woman can have it all.”
And then I read about her desperate attempts to get clout online by claiming to have nearly been a passenger on a flight that crash landed, or using a work trip as an opportunity to promote her book and take the family on vacation, and she felt scandalously human. Through revealing anecdotes about her desperation and greed, she finally felt like one of us, instead of some sort of totem for working women.
Wynn-Williams’ Sandberg is a fragile creature who can be kind and sharp and capricious and cruel. Like this excerpt from the day she met then Japanese Prime Minister Shinzo Abe:
I may have already been looking for evidence to confirm my sense of foreboding but when I arrive at Sheryl’s suite at the Ritz-Carlton the morning of the meeting, I see a stunningly beautiful Japanese woman, perfectly made up and stylishly dressed, quietly crying outside it.
“Are you okay?” I ask tentatively.
She nods. The tears streaming down her cheeks somehow make her even more impossibly lovely.
At that moment Debbie comes bundling out of Sheryl’s suite and pulls me close.
“I wouldn’t go in there.”
“Why?”
“You were going to go in there, weren’t you?”
“Um, yeah—what’s happening?”
“Major issue with the makeup and hair.”
“Is that who’s crying outside the door? The makeup artist?”
“Ah, yeah. The makeup was a disaster and let’s not mention the hair. I mean, I think it was basically fine, but Sheryl hated it and some of her instructions were lost in translation and it’s all come to a head.”
“Or on her head?” I try to pun. Debbie ignores it.
“Oh god. Is it a cultural thing?” I ask. “Like was the makeup artist doing what she thinks Western women want? Quite eighties? It’s still really early. Can you get someone else?”
“Ah, that was the someone else. She already fired the first makeup artist.”
“Ouch. She made her cry too? Okay, so I’m guessing a third makeup artist isn’t going to happen.”
“No, I think she’s going to do it herself, but this does not bode well for the day ahead.”
This is a side of Sheryl I have not seen before.
In this exchange, we don’t even see Sandberg, but we can already see she’s nervous—as anyone would be meeting a head of state. And when she’s nervous, she’s mean. The rest of the chapter retells the meeting, as well as Sandberg’s desperation to get a photo of the Prime Minister holding her book. It reads like a farce of powerful women in business, and I’ll admit to thinking Wynn-Williams was exaggerating.
But here’s that photo of Sandberg and Shinzo Abe. You can see her glee. You can see his amused confusion. You can see she posted this image after he was assassinated as proof that she once met him.
And all of that, while not the image Sandberg seeks to convey, makes her so much more likable. The book gets darker and darker as it goes on and Wynn-Williams realizes just how awful the ramifications of Facebook’s growth-at-all-costs mentality are. But having lived through it all and watching just how terrible Meta’s impact would be on democracy, I found something charming in Sandberg’s humanity.
Sure, she might have helped set up the fall of more than one nation, but she really was just a woman trying to do her best.
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