If the questions makes think, it’s worth asking.
1. What is it like to wake up every morning and pretend that you aren’t dying?
2. Do you believe in the death penalty? What if someone murdered your mother in cold blood? What if someone murdered a stranger’s mother, but saved your life the month before?
3. If you had a friend who spoke to you in the same way that you sometimes speak to yourself, how long would you allow that person to be your friend?
4. Would you rather be rich and paralyzed from the waist down or poor and able bodied?
5. What’s the most expensive gift you have ever received? Is it the best gift you have ever received?
6. When was the last time you lied? Is it possible to lie without saying anything at all?
7. Stealing is immoral, right? But what if stealing was the only way to feed a starving child?
8. If I gave you $20, what percentage would you – really – save? If I gave you $200,000, what percentage would you save? Should there be a difference?
9. If someone could tell you the exact day and time that you are going to die, would you want them to tell you?
10. If you found out you were going to die today, would you have any regrets? Would you be happy with the way you spent the last 24 hours of your life?
11. What’s your single greatest moment of personal failure? Looking back on it now, did it make you weaker or stronger? What did you learn?
12. Do the words ‘freedom’ and ‘liberty’ mean not being persecuted or discriminated against, or do they mean doing whatever you please?
13. Have you ever discriminated against someone? Imagine that a street gang notorious for wearing purple shirts has robbed and murdered several hundred people in your town. If a man wearing a purple shirt just rang your doorbell, would you answer it?
14. Is it crazier to choose to be poor or to spend 40 years of your life hating 40 hours a week?
15. Do you ever feel like you don’t have enough time? How many hours a week do you spend watching TV, or playing video games, or…?
16. Do you ever celebrate the green lights?
17. If you could be given another talent or ability, what would you want it to be? Have you ever – really – tried to perfect this ability in yourself?
18. No matter how bad things get, are you aware that someone always has it worse than you do?
19. When you help someone, do you ever think, “What’s in it for me?
20. Joy is found with simple awareness. What does your joy look like today?
21. What’s the difference between ‘living’ and ‘existing?
22. Are you willing to sacrifice the life of your child or lover to support a war?
23. Do you ask enough questions, or do you settle for what you know?
24. If you could do it all over again, would you change anything?
25. If your life was a novel, what would be the title and how would your story end?
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