1. How do you define success, at least for yourself? Have you reached it? 2. Is there anything you know you should let go of, but you haven’t yet? Why?

3. If you knew this was your last day, would you do the same things you’re doing?

4. What kind of legacy do you want to leave behind? What steps have you taken to create it?

5. If the person who’s hurt you the most showed up at your door, what would you say to them?

6. If you don’t have what you want, what do you have to lose by going after it?

7. What does it mean to be good with money? Are you?

woman thinking while on a balcony hardest questions to answer

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8. Is there anything your job gives you besides money? Is there anything missing?

9. What’s the biggest thing you want to accomplish in the next 12 months?

10. What responsibilities are you avoiding right now or which are you most tempted to avoid?

11. When it comes to your closest relationships, what do you struggle with the most?

12. What mistake do you keep making, and why do you keep making it? What has it cost you?

13. Name something you consider worse than dying. What makes it worse?

14. What’s something you wouldn’t want to die without doing? Why?

15. How would you define the word “American”? How do you define “unAmerican?”

16. If you had three wishes, what would you wish for, and why?

17. What fears are connected to your pursuit of success? How have you faced them?

18. What areas in your life are most in need of improvement?

19. How have your goals or priorities changed over the last decade?

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20. What are your biggest regrets when you think over the past five years?

21. What realization has changed your life or your perspective over the past five years?

22. What is the biggest cause of stress for you right now? What worries you most?

23. Are you too hard on yourself or not hard enough?

24. What do you look forward to the most right now? Why?

25. What do you want to be remembered for when you die?

26. What dream (or dreams) have you given up on? Why?

27. What dream (or dreams) have you held onto the longest?

28. Is there anyone you’re jealous of? If so, why?

29. How are you contributing to the world? Or how do you want to contribute?

30. What is your default behavior when someone turns on you? What has it cost you?

31. When you look at the person you are right now, what are you proudest of?

32. What about yourself do you still need to work on every day? How do you work on it?

33. What have you learned that you might not have learned if you hadn’t suffered?

34. What five words would you use to describe yourself?

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