Discussion questions for Eat the Wind: Travels With Dictators, Mercenaries and Queens

1. The author walked away from a cushy career at a Washington law firm at 28. Did that decision strike you as brave, reckless, or something else? What would you have done in that position?

2. The book is set before the internet changed travel. What did the author gain from traveling without instant information, maps or contact with home? What did he lose?

3. The author says at one point he went six months without seeing a familiar face. Have you ever had a similar experience? Would you be open to that?

4. The author seemed to have a knack for dropping into the middle of major world events. Do you think that was pure luck or somehow earned? Which encounter stood out to you most.

5. If you could go back in time and drop into any of the vignettes retold in the book and live your own version of the story, which would you choose?

6. The author sometimes struggled with balancing the thrill of adventure with the serious human stakes around him. How would you have handled that balance?

7. How did the book’s humor shape your experience of the book? Were there times you felt it was inappropriate or surprised you?

8. The author writes as an older man looking back on his younger self. Where did you sense the biggest gap between who he was and who he became?

9. How do you think these journeys shaped the author’s view of risk and success?

10. Imagine your son or daughter telling you that they were leaving a successful or even elite position to go spend all their money exploring the world. What would your first reaction be, and what would you say to them?

11. What is the furthest ‘off the beaten path” you have ever been? Did it make you want to go still further afield, or did you think “that’s far enough for me?”