Careless People
A former Facebook policy executive gives a candid, sometimes funny, often unsettling insider's account of life inside one of the world's most powerful companies. It's a good pick for a warm evening of honest talk about work, conscience, and the technology in our pockets.
Join us for warm pies, mulled wine, and heartfelt talk about Careless People. Bring your slippers and your stories about the jobs and apps that shaped you.
Best for: Clubs who like a story that sparks heartfelt 'that reminds me of my own job' conversations over a bowl of something warm
Discussion
Warm-up
- 1.Before we open the book, what does your own relationship with Facebook or social media feel like right now: an old friend, a guilty pleasure, or something you've quietly drifted away from?
- 2.The author starts out hopeful that technology could do real good in the world. What were you hopeful about when you first joined a social network, and does any of that hope still linger?
Digging in
- 1.Which moment in the book made you laugh out loud or shake your head, and how did it feel to laugh at something that was also a little alarming?
- 2.The author describes long hours, constant travel, and huge demands while trying to hold a family life together. Did any of her juggling feel familiar to you, and what helped you through your own stretch of 'too much'?
- 3.Have you ever worked somewhere you believed in at first, then started to feel uneasy about? How did the author's experience of that slow shift sit with you emotionally?
- 4.Was there a point where you felt real tenderness or compassion for the author, and was there a point where you wanted to reach into the pages and give her some advice?
Going deep
- 1.The title echoes a famous line about people who break things and let others clean up the mess. After finishing, who did you find yourself feeling most protective of, and why did they stay with you?
- 2.Speaking up can cost a person a lot. Having read the whole story, how did it change the way you feel about the times you've spoken up, or stayed quiet, in your own life?
On the table & to sip
To eat
To sip
Run of show
Host tips
- Some guests may have strong feelings about tech or their own jobs, so gently remind everyone this is a space to share feelings, not win debates.
- Prep the pie filling and pavlova shells the day before so you can relax and enjoy the evening with everyone.
- Put a small basket by the door for phones to add a playful, fitting touch of unplugged coziness.
Playlist
Soft, reflective, and a little wistful, with gentle songs about ambition, power, and finding your way home
- 01 Everybody Wants to Rule the World - Lorde
- 02 Both Sides Now - Joni Mitchell
- 03 Ribs - Lorde
- 04 Fast Car - Tracy Chapman
- 05 Harvest Moon - Neil Young
- 06 Holocene - Bon Iver
- 07 Big Yellow Taxi - Joni Mitchell
- 08 The Times They Are A-Changin' - Bob Dylan
Trivia
- 1.The book's title echoes a famous line from which classic American novel? (The Great Gatsby by F. Scott Fitzgerald)
- 2.Which country is Sarah Wynn-Williams from? (New Zealand)
- 3.In what year was Careless People published? (2025)
- 4.Which publisher released the book? (Flatiron Books)
- 5.What genre best describes Careless People? (Memoir)
- 6.What kind of work did the author do at Facebook? (Global public policy, working as a director on the company's relationships with governments around the world)
- 7.What career did the author have before joining Facebook? (She was a diplomat and lawyer for New Zealand, including work at the United Nations)
- 8.How did Meta respond when the book came out? (It pursued arbitration, and an arbitrator issued an order barring the author from promoting the book, which drew even more attention to it)
Bookmarks
Print, cut, and tuck one at every seat, a small keepsake from the night.
“Some stories are best read with the phone in another room.”
“Big dreams, long days, and a warm cup to come home to.”
“It takes a quiet kind of courage to tell the truth.”
Rate the book
We hope the company was good and the conversation even better. Until the next chapter.