Careless People
by Sarah Wynn-Williams

Careless People: Chapter 36 Summary & Analysis

Summary
Analysis
A frustrated Zuckerberg wants to play board games on his private jet. But when Wynn-Williams beats him at Ticket to Ride and Settlers of Catan, he accuses her of cheating. Wynn-Williams points out how Zuckerberg actually had multiple ways to win at Catan but made the wrong moves. Against Wynn-Williams’s better judgment, she turns this into a conversation about how in general, Zuckerberg made the wrong choices with Facebook. He admits that Wynn-Williams makes a fair point about how he should have changed the name of Internet.org earlier.
The way that Wynn-Williams beats Zuckerberg at these board games shows how he is fallible and doesn’t realize the limits of his own skills. In particular, the way that Wynn-Williams points out to Zuckerberg how he could have won at Settlers of Catan reflects how she believes he has also made bad leadership decisions at Facebook, where things could have gone in a different, better way.
Active Themes
Carelessness, Wealth, and Greed Theme Icon
Zuckerberg has been focused a lot on his legacy recently, and one part of it is a commencement speech he’s giving at Harvard in a few months. He starts talking about plans in 2017 to visit as many states as possible and meet people there, which surprises Wynn-Williams, since Zuckerberg has never much liked travel or people. As Wynn-Williams hears the states Zuckerberg wants to visit, she realizes he’s considering a run for president. She tries to tell Elliot that this is a bad idea, but Elliot doesn’t feel it’s their place to intervene.
Zuckerberg’s decision to run for president shows how his ego has begun to drive his actions even more than before. It perhaps also suggests that he is looking for other things to focus on to distract him from the current challenges he faces at Facebook. Elliot has at times been a voice of reason who talked Zuckerberg out of bad ideas, and Elliot backing down reflects how Facebook is increasingly driven by Zuckerberg’s careless whims.
Active Themes
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Bureaucracy and Obstacles to Change Theme Icon
Zuckerberg doesn’t want to collaborate with traditional media. He wants a new order with Facebook at the heart of the news ecosystem to help fix it. Wynn-Williams is shocked at how abruptly Zuckerberg seems to have changed his goals in life from what they were just 48 hours ago before Peru.
Active Themes
Carelessness, Wealth, and Greed Theme Icon
All of this takes place over the course of one private jet ride, and as the plane descends, Wynn-Williams knows this is the last trip like this that she can take with Zuckerberg. She sees him going down a different path and doesn’t want to be part of it. At one point, Zuckerberg asks Wynn-Williams what she thinks, and all she can think to reply with is, “Rosebud.” Immediately, she realizes that this was a bad idea and that Zuckerberg doesn’t understand at all. Elliot tries to explain the plot of Citizen Kane and how William Randolph Hearst tried to control the publishers and run for office at the same time. Zuckerberg asks if this was a bad thing, and no one is sure how to answer. One the tarmac, he says, “Good trip, everyone. Lots to think about.”
Active Themes
Carelessness, Wealth, and Greed Theme Icon
Idealism and the Failed Promises of Technology Theme Icon
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