BOOK REVIEW: CARELESS PEOPLE

Careless People

Sarah Wynn Williams

Flatiron Books

400 p.

Sarah Wynn-Williams, former Facebook director of global public policy, did one thing right when she opened her memoir with the famous F. Scott Fitzgerald quote, “they were careless people, Tom and Daisy – they smashed up things and creatures and then retreated back into their money or their vast carelessness or whatever it was that kept them together, and let other people clean up the mess they had made.”

“Careless People” is a version of a modern Gatsby, for all the reasons Wynn-Williams thinks it is and a few reasons she probably doesn’t. The memoir reads like a window into the elite between the private planes, extravagant parties, and inexperienced people handed extraordinary power. But it is told through a pretty unreliable narrator.

That’s mainly because Wynn-Williams worked for Facebook from 2011 to 2017 and occupied positions of influence throughout. She attempts to hold herself accountable, but nearly every chapter begins and ends with a story about how she tried to stop the company, redirect leadership or warn executives before things spiraled further. 

It reminds me of the episode of Gilmore Girls where Rory, after having her prep school and Yale education bankrolled by her wealthy family, writes a scathing article mocking the privilege and extravagance of her peers.

It’s probably true. I just don’t fully trust her to tell me.

What the book asks well is not whether readers believe every allegation Wynn-Williams makes against Facebook, but whether anyone should hold that kind of power at all, regardless of how responsibly they claim to wield it.

For that reason alone, the memoir is worth reading.

Her story begins with a memory of being bitten by a shark at age 13. The wounds become infected, leading to sepsis, and she nearly dies. Wynn-Williams frames the experience as proof that she possesses the resilience and luck necessary to do something meaningful with her life.

She first finds that meaning working at the United Nations. But as a New Zealander, she feels sidelined and unable to accomplish much. Watching Facebook expand across the United States, she becomes convinced that its executives do not fully understand the scale of what they are building or the influence they are about to wield globally.

She repeatedly pushes Facebook to create a position dedicated to working with foreign governments. At first, they refuse. By her account, leadership is interested primarily in growth, not public service or democratic responsibility. Only after she explains that Facebook became the primary way she communicated with her sister following a devastating earthquake in New Zealand does the company soften and hire her.

Wynn-Williams’ criticisms of Facebook are ultimately twofold. First, she describes a workplace culture that demands relentless loyalty from employees, particularly women, while treating family life and personal boundaries as obstacles to productivity. 

Second, she portrays a Silicon Valley tech company so obsessed with expansion that it steamrolls countries, particularly those with limited digital infrastructure, into surrendering privacy and political stability in exchange for connectivity.

On the latter front, for example, she points to Facebook’s willingness to work closely with authoritarian or semi-authoritarian governments to expand access, even when those governments could use the platform for surveillance or political manipulation.

According to the book, Facebook explored creating moderation and censorship systems that would comply with Chinese government demands, including the possibility of a “chief editor” who could remove content or even shut down the platform during periods of unrest.

She also criticizes Facebook’s “internet.org” initiative, later renamed “Free Basics,” which promised internet connectivity to countries with limited digital infrastructure.

Wynn-Williams describes Facebook mobilizing its own users as a lobbying force in India during debates over Free Basics and net neutrality. 

The company encouraged users to send pre-written messages to regulators supporting the service after the Telecom Regulatory Authority of India moved toward restricting differential pricing for internet platforms. According to Wynn-Williams, once a user sent the letter, notifications would be pushed to friends suggesting they had. At times, the messages were reportedly sent even when users had not actively submitted the letter.

On the workplace side, Wynn-Williams frames many of her experiences through the culture surrounding the philosophy of her boss, Sheryl Sandberg, “Lean In,” which encouraged women to push through pregnancy and motherhood without allowing those realities to interfere with professional ambition.

She recounts incidents involving Sandberg’s staff that she describes as deeply inappropriate and emotionally invasive, including claims that assistants were tasked with purchasing expensive lingerie and expected to maintain unusually blurred professional boundaries. 

Wynn-Williams recounts an uncomfortable moment in which Sandberg allegedly invited her to “come to bed” during a trip and sneered when she declined.

Throughout the memoir, Wynn-Williams describes her belief in Facebook as a democratic “revolution” gradually collapsing as she watches the company prioritize growth over nearly every other concern.

That interpretation has drawn mixed reactions from former colleagues.

“I can say that the meetings and events I was a part of that are recounted in the book (and things that were relayed to me by others contemporaneously) are accurately represented,” her former coworker, Brooke Oberwetter, wrote. “Sarah wasn’t the only one who felt the way she felt going in–optimistic, hopeful, lucky, proud, hoping to do good–and the way she felt going out–disappointed, demoralized, disillusioned, and exhausted.”

However, former Facebook public policy director Katie Harbath disputed Wynn-Williams’ account, writing that “Sarah’s book is riddled with factual inaccuracies and exaggerations.”

After the book was published last year, Meta responded aggressively to the memoir’s publication, pursuing emergency arbitration against Wynn-Williams and temporarily barring her from promoting the book, arguing she violated non-disparagement agreements signed after leaving the company.

It may never be fully clear whether every detail in Wynn-Williams’ account is accurate. But the unsettling part is not the uncertainty itself, but how plausible so much of it feels.