Careless People Reading Guide & Discussion Questions

1. Careless People begins with a quote from The Great Gatsby. How do you think this sets the stage for the rest of the book? Did the epigraph have an impact on how you approached reading what followed?
2. Sarah Wynn-Williams writes that her career at Facebook "started as a hopeful comedy and ended in darkness and regret." What did you think of this statement? Are there examples of each extreme that stand out to you?
3. The author began considering working for Facebook in 2009, "in those innocent days when it still was possible to be hopeful about the internet." What do you remember about your first experiences of the internet or social media? What has changed over the years, and what hasn't?

Unless otherwise stated, this discussion guide is reprinted with the permission of Flatiron Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.