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If the question makes you think, it’s worth asking.
- What is it like to wake up every morning and pretend that you aren’t dying?
- 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?
- 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?
- Would you rather be rich and paralyzed from the waist down or poor and able bodied?
- What’s the most expensive gift you have ever received? Is it the best gift you have ever received?
- When was the last time you lied? Is it possible to lie without saying anything at all?
- Stealing is immoral, right? But what if stealing was the only way to feed a starving child?
- 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?
- If someone could tell you the exact day and time that you are going to die, would you want them to tell you?
- 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?
- 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?
- Do the words ‘freedom’ and ‘liberty’ mean not being persecuted or discriminated against, or do they mean doing whatever you please?
- 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?
- Is it crazier to choose to be poor or to spend 40 years of your life hating 40 hours a week?
- 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…?
- Do you ever celebrate the green lights?
- 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?
- No matter how bad things get, are you aware that someone always has it worse than you do?
- When you help someone, do you ever think, “What’s in it for me?”
- Joy is found with simple awareness. What does your joy look like today?
- What’s the difference between ‘living’ and ‘existing?’
- Are you willing to sacrifice the life of your child or lover to support a war?
- Do you ask enough questions, or do you settle for what you know?
- If you could do it all over again, would you change anything?
- If your life was a novel, what would be the title and how would your story end?
