1. We all learn from our mistakes, yet we’re always so afraid to make one. Where is this true for you?
2. What risk would you take if you knew you could not fail?
3. What is your greatest strength? Have any of your recent actions demonstrated this strength?
4. What are the top five things you cherish in your life?
5. How old would you be if you didn’t know how old you are?
6. When do you stop calculating risk and rewards, and just do it?
7. At what time in your recent past have you felt most passionate and alive?
8. What do you most connect with? Why?
9. What one piece of advice would you offer a newborn child?
10. Which is worse—failing or never trying?
11. Why do we do things we dislike and like the things we never seem to do?
12. What are you avoiding?
13. What is the one job/cause/activity that could get you out of bed happily for the rest of your life? Are you doing it now?
14. When it’s all said and done, will you have said more than you’ve done?
15. What are you most grateful for?
16. What would you say is one thing you’d like to change in the world?
17. Do you find yourself influencing your world, or it influencing you?
18. Are you doing what you believe in or settling for what you’re doing?
19. What are you committed to?
20. Which worries you more – doing things right or doing the right things?
21. If joy became the national currency, what kind of work would make you wealthy?
22. Have you been the kind of friend you’d want as one?
23. Do any of the things that used to upset you a few years ago matter at all today? What’s changed?
24. Would you rather have less work to do or more work you enjoy doing?
25. What permission do you need/want to move forward?
26. Really, what do you have to lose if you go for it?
27. How different would your life be if there weren’t any criticism in the world?
28. We’re always making choices. Are you choosing for your story or for someone else’s?
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