In the past few months I have noticed a steady uptick in a particular type of message from friends and acquaintances. It is the “I think it is time to move on” email, WhatsApp or LinkedIn private message, quietly asking for a coffee and a chat. They are coming – not exclusively, but primarily – from people working in tech.
There is a mood of quiet unease out there in the land of suddenly less fancy in-house canteens. This is no doubt contributing to the success of a new tell-all memoir by former Facebook executive Sarah Wynn-Williams, and why I had to visit multiple bookshops to track down a copy of Careless People: A Story of Where I Used to Work.
The book landed without much warning, perhaps an attempt to get it out into the world before the lawyers could shut it down. Perhaps this was even a subversion of Tech World’s “move fast and break things” approach to making facts on the ground that then have to be dealt with.
Either way Meta, Facebook’s parent company, managed to get an order blocking Wynn-Williams from promoting the book, but did not succeed in getting the book itself taken off the shelves. What better marketing strategy can you have in 2025 than “being silenced”?
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Careless People is very readable, and you get the sense that Wynn-Williams, a one-time junior New Zealand diplomat turned Facebook lobbyist, would be a very entertaining dinner party guest. It is a collection of well honed anecdotes from her seven or so years helping the company figure out how it engaged with governments around the world.
The endless name-dropping – from dancing near Hillary Clinton at a Colombian salsa club, to mixing with cultural megastars such as Beyoncé and parties at Davos with our own Enda Kenny – is usually juxtaposed with stories of just how inept and/or callous the leaders of the company were.
Storytelling is perhaps the strongest currency in Silicon Valley, where company valuations can rely as much on the origin stories of founders and fantastical tales of future growth as on any rational assessment of business fundamentals. The author of the Financial Times’s Lex column recently stated that for companies such as Nvidia and Palintir, “80 per cent of the value comes from things that happen after 2030″, or, put another way, from the stories these companies tell about that future.
Wynn-Williams’s book uses storytelling to make pointed critiques of this very culture, yet falls into some of the same traps. A story is not an analysis. (For that you would do better to tune into the likes of historian Jill Lapore’s excellent new podcast series X Man: The Elon Musk Origin Story).
The central thesis of this book is that Facebook – the product and the company – had enormous potential, but people – a small handful of people – messed it up. Three very well known executives are singled out for blame: Mark Zuckerberg, who is presented as controlling and aloof; Sheryl Sandberg, who is portrayed as vain and manipulative; and Joel Kaplan, who comes in for the sharpest criticism, including accusations of inappropriate behaviour.
While these portrayals are not especially new, Wynn-Williams’s proximity to these people combine with her power with the pen to bring these caricatures into startling, damning, technicolour light. (Meta has characterised the book as “a mix of out-of-date and previously reported claims about [Meta] and false accusations about our executives”).
The author is very explicit about pinning blame on these individuals. In her closing arguments she states: “It really didn’t have to be this way ... something else was possible. They really could have chosen to do it all differently”. When you present the story of Facebook as one of merely people making bad decisions based on moral weaknesses, you ignore the wider context of an industry that systematically rewards companies that let these kinds of people rise to the top.
Facebook wasn’t ruined by careless people, Facebook grew into what it was, and then what it is, because ruthless, growth-oriented careless people were in charge.
This line of thinking also implies that if people caused these problems, then maybe people could have fixed it. The arc of the book is one of personal disillusionment, how Wynn-Williams “told myself I could do more on the inside than the outside”.
That echoed the refrain I heard repeatedly from digital rights activists through the late 2010s as they were recruited in their droves by companies such as Facebook and Google. These smart, committed and capable people had been advocating for tech companies, and the governments who were failing to regulate them, to do better.
The activists turned tech workers got impressive-sounding job titles, and signed non-disclosure agreements (NDAs). From one conference to the next, brilliant advocates from across the world went from speaking out to handing out branded merch and cocktails at fancy corporate drinks receptions.
Many no doubt did difficult and underappreciated work to try to make these companies better. They will have had some real wins. But they were never going to have any real power inside corporate behemoths that prize growth above all else. As the tech oligarchy pivots to appease an increasingly authoritarian White House, many of this wave of hires are no doubt coming to the same conclusion as Wynn-Williams, that “being the grit in the machine wasn’t working”.
In the end Wynn-Williams didn’t leave the company of her own volition. She was let go for “poor performance”, something she portrays as a vindictive response to her HR complaints against executives. Her immediate concerns are for the big house she has purchased, the golden handcuffs of tech salaries that, along with the NDAs that employees sign, make leaving and speaking out as she has done very difficult. The financial and legal power that tech companies possess is as much a force against its own staff as it is against regulators’ attempts to tame it. Careless People is an entertaining act of resistance against that power but does little to challenge the system that enabled it.
