1. How much did you know about the prison system in the United States before reading this book? What was the most surprising thing you learned?
2. Of the primary characters, whom do you think was most affected by asynchronicity? Who was released into a world most similar to the one they had left? If you were imprisoned today, which aspect of your life would make you feel most “left behind”?
3. Compare Vicki’s short but frequent incarcerations to a long sentence like Arnoldo’s or Dave’s. How does recidivism impact someone’s support system?
4. In your opinion, which character had the most successful transition from prisoner to citizen? What were the most important resources they used to achieve that success?
5. Arnoldo and Sterling are both deeply involved with restorative justice (RJ). Discuss the ways they apply RJ and conflict resolution. How do these practices shape their ongoing experiences? How would you use RJ to help someone like Trevor, who faced extreme community backlash after his release?
6. Vicki’s reentry has been especially complicated, and Kessler specifically avoids learning some details as a sign of support. If you followed your first impulse, what would you have done in Kessler’s position? Do you think your strategy would change any of Vicki’s outcomes?
7. Kessler describes each character’s outfit upon release. How do your clothes communicate your identity? How do each ex-prisoner’s clothes reflect the conditions they will meet out in the world?
8. Some of the characters were tried as adults for crimes they committed as teenagers. Should children under eighteen ever be tried as adults? How does that practice influence long-term rehabilitation outcomes?
9. In your opinion, what is the biggest obstacle to successful reentry? Can you think of a solution?
10. There is some debate about the purpose of imprisonment. What purpose do you think prisons are currently serving? What purpose should they serve? Name three changes you would make to enact the purpose you’ve identified.