Careless People: A Chapter-by-Chapter Analysis
Author: Sarah Wynn-Williams (Former Director of Global Public Policy at Facebook) Publication Date: March 11, 2025 (Flatiron Books / Macmillan)
Subtitle: "A Cautionary Tale of Power, Greed, and Lost Idealism"
This book is Wynn-Williams's memoir of her time at Facebook (now Meta) from 2011 to 2017. Through her firsthand experiences, the author exposes Facebook's internal culture and decision-making processes, revealing how the tech giant transformed from an idealistic, innovative platform into an empire that wielded global influence while "carelessly" abusing its power. The title, Careless People, is a direct quote from the final line of the American classic The Great Gatsby: "They were careless people." The original line refers to the wealthy and indifferent Tom and Daisy Buchanan. Wynn-Williams draws a parallel to Facebook's founder Mark Zuckerberg and COO Sheryl Sandberg, who are portrayed in the book as modern-day counterparts to Tom and Daisy, recklessly destroying people's lives and retreating into their vast wealth, leaving others to clean up their mess. This metaphor, rooted in the decadent Gilded Age of 20th-century America, highlights the indifference and imbalance of power and responsibility among modern tech leaders.
This report will provide a chapter-by-chapter summary, focusing on each chapter's main themes, key events and figures, and the compelling historical anecdotes, social details, and character portraits within the book. We will also examine the intersections of 20th-century American history and contemporary reflection, such as the author's use of historical allusions (classic literature, political figures, cultural symbols) to mirror the realities of the modern social media era. Without delving into other works or the author's writing style, the following is a breakdown of Careless People:
Chapter 1: The Call of Idealism – From Diplomat to Social Media Pioneer
Theme: The author's transition from a New Zealand diplomat to a Silicon Valley idealist. Wynn-Williams describes how, in the early 2010s, she was driven by the idealistic potential of social media to connect the world. This belief led her to leave her traditional diplomatic career and proactively seek a position at the rapidly growing Facebook. Having worked at the United Nations and the New Zealand Embassy in the U.S., she felt like a mere cog in a bureaucratic machine and yearned for a more impactful role. In 2011, as a young international lawyer and diplomat, she pitched herself to Facebook, even designing the role of "Director of Global Public Policy" because the company's leadership had not yet realized they needed such an expert. She recalls the difficulty of even getting in touch with Facebook, describing the company as a "brick wall," but she managed to "pry open a crack" through her network and land the job. This journey underscores her passionate belief in Facebook's mission.
Core Events & Details: This chapter establishes the author's motivation for joining Facebook. Wynn-Williams recounts a personal experience that solidified her belief that social media could be a force for good: during the 2011 Christchurch earthquake in New Zealand, she temporarily lost contact with her sister, who was in the disaster zone. She was immensely relieved to learn of her sister's safety the next day via Facebook. This event deeply moved her, demonstrating the value of global connectivity and real-time information and fueling her ambition to join Facebook to advance its vision of a connected world. With this conviction, she left her stable government career for the uncertainty of Silicon Valley, hoping to "make a difference at a pivotal moment in history." The chapter sets an idealistic tone, portraying her belief that Facebook had the potential to break down borders and unite people, with her determined to be a guiding force.
Character Introductions: The author briefly introduces herself (New Zealand origin, background in law and diplomacy) and Facebook founder Mark Zuckerberg. She notes that Zuckerberg, then in his late 20s, led a team of geeks and engineers and was surprised by her unsolicited pitch. However, her persistence and expertise won them over, and she became the company's first executive dedicated to global policy and government relations, setting the stage for her future advocacy on global issues within Facebook.
Chapter 2: Silicon Valley Initiation – An Empire of Engineers and "Little Red Book" Culture
Theme: The author's initial impressions of Facebook's headquarters, depicting its unique corporate culture and power structure. Upon arriving in Silicon Valley, Wynn-Williams found a company dominated by young software engineers and "frat boys" who were flush with cash and operated with impunity. The work environment felt more like a college dorm than a traditional corporation. Facebook had transformed from a Harvard campus social network into a global information empire in just a few years, yet its culture retained a youthful arrogance. This chapter highlights the duality of the internal culture: on one hand, an innovative energy and wealth explosion that stunned outsiders; on the other, highly centralized decision-making and a near-fanatical corporate ideology.
Core Content: Wynn-Williams observed an "engineers-first" philosophy where programmers and tech experts held the reins of power. As the newly appointed Director of Global Public Policy, she was astonished to find that the top leadership, especially Zuckerberg, had almost no interest in international politics or diplomacy and even disliked attending diplomatic functions. She describes Zuckerberg at the time as a tech prodigy holed up in his lab, focused solely on product features and user growth, and dismissive of government affairs and international relations. This made her initial work challenging, as she had to persuade this group of "tech bros" of the importance of a global perspective.
Social Details: The author uses vivid anecdotes to illustrate Facebook's peculiar culture and the narrow geographical awareness of some Americans. For instance, a senior executive was clueless about New Zealand's location, much to her amusement and dismay. She jokingly offered to buy him a world map for his office. He initially declined, but shortly after, a large world map appeared on his wall. This anecdote is both humorous and telling: Facebook's decision-makers, despite their global impact, knew little about the world and needed a basic lesson in international geography.
Corporate Culture: The "Little Red Book" Phenomenon: Wynn-Williams describes a legendary employee handbook, jokingly referred to as Facebook's "Little Red Book." Much like Mao's Little Red Book for the Red Guards, Facebook's version compiled the quotes, photos, and core philosophies of its "supreme leader," Mark Zuckerberg. New employees received a copy to learn the company's values. She quips, "Of course, the 'Chairman' in this book wasn't Mao, but Mark." This half-joking comparison highlights the personality cult and ideological nature of Facebook's corporate culture. The company fostered a quasi-religious atmosphere where the words of the leadership were gospel, and all employees were expected to memorize and adhere to them. The historical parallel between 20th-century Maoist doctrine and 21st-century "Markisms" reveals the fervor and insularity of Facebook's internal culture, where decisions were heavily influenced by Zuckerberg's personal will.
Engineers Rule and Gray Areas: In the latter part of the chapter, the author points to a worrying aspect of Facebook's culture—a disregard for rules and a willingness to operate in gray areas. The engineer-led management championed moving fast and breaking things, adopting a utilitarian approach to law and policy: one set of principles for public consumption, while privately exploiting loopholes and pushing boundaries. She gives an example of the company publicly committing to protecting user data privacy while privately allowing developers to operate freely in policy gray areas. This double standard would pave the way for a series of future scandals and began to raise her alarm about the dangerous tendencies within Facebook's culture.
Chapter 3: A Stumbling Global Expansion – The First Taste of Power
Theme: This chapter chronicles Facebook's initial forays into the international diplomatic arena and the author's role in it. Between 2011 and 2012, as Facebook transitioned from a campus product to a global platform, it began tentatively engaging with world leaders. As Director of Global Public Policy, Wynn-Williams actively arranged meetings for Zuckerberg with international dignitaries to enhance the company's legitimacy with foreign governments. Zuckerberg was initially indifferent to such events until he got a taste of the political spotlight, which gradually changed his attitude. The chapter focuses on Zuckerberg's initial encounter with political power, tracing his transformation from awkward shyness to burgeoning ambition.
Core Event 1 – First Meeting with a Head of State (Russia, 2012): In 2012, Zuckerberg met his first sitting head of state: Russian Prime Minister Dmitry Medvedev. Wynn-Williams, who was present, described Zuckerberg as being so nervous that he was sweating profusely. This meeting was a new experience for the young Silicon Valley entrepreneur; for the first time, he realized that as the head of a social media empire, he could sit as an equal with political strongmen. Transitioning from unease to savoring the sweetness of power, Zuckerberg began to develop an interest in high-level diplomatic events. Wynn-Williams notes that Zuckerberg developed a taste for it: he started requesting to meet more legendary figures at international gatherings. For example, he tried to be seated next to Cuban leader Fidel Castro at a dinner (a request that was not fulfilled). Zuckerberg became captivated by the feeling of being on the world stage, shoulder-to-shoulder with influential figures. He had tasted power, and his ambition grew.
Core Event 2 – Expanding into Emerging Markets (Myanmar, 2012): During the same period, Facebook extended its reach to countries with low internet penetration. The chapter details a symbolic diplomatic mission: in October 2012, Wynn-Williams was sent to Myanmar to negotiate with senior military government officials to lift the block on Facebook. At the time, Myanmar was just beginning its democratic transition, but online speech was still controlled by the military. Facebook had been banned, and her mission was to lobby the military junta to "unban" Facebook, allowing the American social product into a new market. She successfully persuaded the Myanmar authorities, opening the country to Facebook. Ironically, the author would later discover that local civil society activists had warned her as early as 2012 about the growing problem of hate speech on the platform, but the company was indifferent at the time. The book later details the tragic consequences of this negligence (the Rohingya genocide), but here it serves as foreshadowing. At the moment, Facebook viewed its entry into Myanmar as a victory, focusing on expanding its territory without anticipating that the platform would later be used to "incite hatred and violence."
Social Details: The author wryly describes her role as Facebook's "diplomatic pioneer," traveling the world to get governments to accept this new American platform. In promoting it in new markets, she sometimes encountered comical situations. The book mentions that Myanmar officials at the time had almost zero understanding of Facebook, leading to numerous misunderstandings and cultural clashes during their talks. For instance, some military officials were baffled as to why young people were so keen on sharing trivial details of their lives online, while the author emphasized how Facebook could facilitate information dissemination and economic development. The military government was ultimately persuaded, partly because they saw Facebook as a potential tool for monitoring public opinion (which also sowed the seeds of future chaos in Myanmar).
Historical Parallel: Wynn-Williams's descriptions subtly evoke the rise of early 20th-century multinational corporations like Standard Oil and the East India Company. As a new kind of information-age enterprise, Facebook's global expansion similarly involved striking deals with local powers and influencing sovereign policies. Her personal experience shows that tech companies had become powerful enough to negotiate directly with governments, a privilege previously reserved for superpowers or multinational conglomerates. Facebook, as a 21st-century social empire, was mirroring the imperialist expansion of the past, only this time conquering digital territory.
Chapter 4: Privileged Flights – A Daily Life of Private Jets and Lavish Perks
Theme: This chapter shifts focus to the extravagant lifestyle of Facebook's top executives and the company's hierarchical culture of privilege. Traveling frequently with senior management, Wynn-Williams experienced flying around the world on private jets and witnessing scenes of extreme luxury. This was a stark contrast to her previous life in the public sector; no matter how demanding her diplomatic work had been, it never approached the opulence of Silicon Valley's tech giants. Through her firsthand accounts, she exposes the lavish spending of Facebook's leadership, implying a moral numbness brought on by immense wealth.
Descriptions of Luxury: In the author's telling, the private jet trips of Facebook executives were astounding: the planes were equipped with bedrooms, a wide array of fine food and entertainment, and top executives could party or negotiate deals at 30,000 feet. During one intercontinental flight, she witnessed a few executives hatch an audacious plan, as if their billion-dollar fortunes made anything possible. For example, she mentions that some "crazy ideas were green-lit on private jets," with Facebook's decisions affecting hundreds of millions of people being made by this small, exclusive circle. This highlights the concentration of power and arbitrary decision-making: when decision-makers are detached from reality in a vacuum of luxury, they are more likely to make far-reaching decisions carelessly. As the author notes, many of Facebook's later, more outrageous projects were "cooked up" in this environment.
Privilege and Detachment: The author laments that Facebook's leadership, living in a bubble of privilege, grew increasingly disconnected from the reality of ordinary users. She recounts a specific detail: on a business trip aboard a company private jet, she saw firsthand how executives squandered company funds. The wine budget for a single in-flight meal ran into thousands of dollars. At the same time, the platform was filled with stories of real suffering from users around the world, creating a jarring sense of irony. This chasm between the haves and have-nots planted a seed of doubt in her mind: Did Facebook's leaders, who claimed to be connecting the world and empowering people, truly understand the needs of the masses? Or were they living in their own luxurious bubble?
Related Figures: This chapter also provides background on some of Facebook's early key executives. For example, she mentions figures from the American political establishment, with Joel Kaplan being a prime example. Kaplan, a former Deputy Chief of Staff in the George W. Bush administration, had deep connections in Washington, D.C. In 2011, Facebook hired him as Vice President of U.S. Public Policy. He was later promoted to Vice President of Global Public Policy, becoming the author's boss. These figures, who moved seamlessly between politics and business, brought Republican-style connections and hardball tactics to Facebook, adding a "D.C. power-player" element to its culture. Through descriptions of the exclusive gatherings on private jets, the chapter underscores the insular and echo-chamber effect of Facebook's inner circle—a few like-minded individuals with aligned interests controlled everything, their world vastly different from that of their users.
Chapter 5: The Geometry of Power – Gray Games in a Small Circle
Theme: This chapter delves into the small-circle culture of Facebook's power core and how the company operated in the gray areas of regulation and rules. The author reveals that Facebook was manipulated by a small, incestuous group of people who controlled the attention of billions. This circle had its own logic: highly cohesive internally, while adopting aggressive and even unscrupulous tactics to protect its interests externally. Wynn-Williams concludes from her observations that Facebook's leadership was power-hungry and lacked checks and balances, gradually creating a situation of unchecked authority.
Core Argument – Concentration and Expansion of Power: The author points out that Zuckerberg's special share structure gave him veto power, granting him absolute control over the company. Although Facebook was a publicly traded global company, it effectively operated like a private empire—"Facebook is a dictatorship run by one man." She reveals that the company's annual filings with the U.S. Securities and Exchange Commission (SEC) explicitly stated this: Zuckerberg could unilaterally sell the company or change its direction, even against the wishes of the board and other shareholders. This meant that Facebook's decisions often reflected Zuckerberg's personal obsessions. For example, he long viewed explosive user growth as the ultimate goal, like a chess master focused only on winning, and was willing to use aggressive means to achieve it. The author emphasizes that company policy always followed Zuckerberg's preferences: whatever he was obsessed with, the entire company's resources would shift in that direction.
Operating in "Gray Areas": Under this structure, Facebook demonstrated a flexibility that bordered on lawlessness in its global expansion. Wynn-Williams reveals several secret projects. For instance, in 2014, the company formed a "China team" dedicated to developing a version of the platform that complied with Chinese censorship requirements to enter the market. In 2015, the company even developed a censorship system tailored for Chinese authorities, allowing a designated "editor-in-chief" to delete posts and, if necessary, shut down the entire site with a single click. These plans were never made public at the time; the company claimed it would "not sell out its values to enter China," while privately building a mechanism for full compliance with censorship. Similarly, Facebook executives discussed lowering privacy protections for users in Hong Kong and forming joint ventures with Chinese companies to bypass restrictions. These seemingly unthinkable compromises demonstrate Facebook's willingness to cross ethical red lines in the pursuit of profit. It was only in recent years, as U.S.-China relations deteriorated and Washington became hostile toward China, that these China-related projects were halted. The author's revelations in the book and subsequent whistleblower complaint to the SEC confirmed that Zuckerberg had long tried to "cooperate with the Chinese government," and had even preemptively enabled some censorship tools for trial use by CCP officials in places like Hong Kong and Taiwan.
Historical Metaphor: The author laments that tech giants like Facebook are no different from traditional industrial behemoths—they are the oil and tobacco tycoons of the digital age. She writes, "It struck me that Meta and its peers were just digital versions of the oil, mining, and tobacco conglomerates of the past." These companies were also greedy, suppressed dissent, and were even willing to collude with authoritarian regimes in exchange for market access. The only difference is that the resource they control is human attention and speech, not a tangible product. Through these inside stories, the author emphasizes that when the power of tech giants is highly concentrated and lacks checks and balances, the harm they can cause is comparable to that of the most notorious corporate empires of the 20th century.
Chapter 6: A Mirage – The Illusion of Female Empowerment and the Truth About Sandberg
Theme: This chapter focuses on the gender dynamics within Facebook and the dual identity of Sheryl Sandberg. As one of the few women in senior leadership, Wynn-Williams initially saw Sandberg as a role model—Sandberg's 2013 bestseller, Lean In, encouraged women in the workplace to assert themselves. However, as they worked together, she gradually saw the disconnect between Sandberg's words and actions. The so-called female empowerment was merely a facade at Facebook. This chapter reveals Facebook's true attitude toward women in the workplace and the disappointing reality behind Sandberg's "powerful career woman" persona.
The Reversal of Sandberg's Image: Wynn-Williams recounts her initial admiration for Sandberg. The 2013 publication of Lean In sparked a global conversation about gender equality in the workplace, and Sandberg was celebrated both inside and outside Facebook as a symbol of female leadership. She promoted a "Lean In" culture within the company, encouraging female employees to actively seek promotions. However, the author soon discovered that Sandberg's support for women was purely rhetorical. In reality, she demanded absolute obedience and personal loyalty from her subordinates. Wynn-Williams sharply describes Sandberg's management style: "She marketed 'leaning in,' but underneath was an unspoken rule—obedience and closeness." In other words, Sandberg wanted female employees to emulate her, but only if they played by her rules and remained loyal to her.
Shocking Anecdotes – Luxury Lingerie and an Invitation to "Sleep Together": The author uses two startling personal stories to expose Sandberg's boundary-crossing behavior and peculiar power dynamics. In one instance, Sandberg instructed her 26-year-old female executive assistant to purchase high-end lingerie for both herself and Wynn-Williams, with an unlimited budget. The absurd shopping trip ended up costing $13,000. The author felt deeply uncomfortable: a superior asking a subordinate to buy intimate apparel clearly crossed professional boundaries. In another incident, during a business trip to Europe, Sandberg's actions were even more shocking. They were on a 12-hour flight from Europe back to the U.S. on the company jet. Sandberg, dressed in pajamas, occupied the only sleeper bed on the plane and repeatedly ordered Wynn-Williams to "come sleep with me." The author declined several times, and Sandberg seemed displeased. This scene made the author feel unprecedented pressure—as if Sandberg were testing, or even toying with, her subordinate's obedience. Wynn-Williams later confessed to a friend that the request made her extremely uncomfortable, but it was difficult to refuse in such a power-imbalanced situation.
Disordered Superior-Subordinate Relationships: The relationship between Sandberg and her young female assistant also displayed an overly intimate and strange dynamic. The author describes an instance during a long trip in Europe where Sandberg and the assistant took turns napping with their heads on each other's laps in a car, stroking each other's hair to sleep. This behavior went far beyond a typical boss-employee relationship and left the author, who was present, stunned. She began to suspect a severe disconnect between Sandberg's actions and her public image—onstage, she advocated for a professional image for women, while offstage, she engaged in power games resembling cronyism.
The Plight of Women in the Workplace: While reflecting on Sandberg, Wynn-Williams also points out some of the double standards women faced at Facebook. For example, although the company promoted "diversity and inclusion," many female employees felt objectified and marginalized. Facebook's culture was rife with a male-dominated "frat boy" atmosphere, and women who didn't conform or play along found it difficult to break into the senior circles. The author's own experiences as a working mother (detailed in a later chapter) further proved that Facebook was not truly friendly to women and families. She gradually realized that Sandberg's success was more about personal branding than about improving the situation for women at large.