• What would you do more of if there weren't any consequences?
• What would you do even if you were guaranteed to fail?
• What is your best case scenario, what's the dream?
• What is something you believe to be true that most other people do not?
• If you had to be stuck in one grade in school in an endless loop which one would you pick?
• Which two people would you most want to listen to have a 3 hour conversations?
• What would you want to have a 3 hour conversation about?
• What is one question that’s currently a mystery that you would want to know the answer to?
• You could buy memories of a trip rather than actually going on the trip, would be nearly indistinguishable in hindsight, would you do it?
• Do you believe in American exceptionalism?
• Was it immoral to bring Nazi scientists to the US in operation paperclip?
• If you had to hand pick a benevolent dictator to rule the US who would it be?
• If you were emperor for a day and implement two rules what would they be?
• There is a gifted individual who knows how to connect with people. He can either be a therapist to 200 people or build an app that impacts 200k+. The underlying question is whether you would rather have a direct impact on a few people or an indirect, but equally large aggregate impact on 200k+. What if you're much happier in the former but have a greater impact in the latter? At what point is the trade-off between your misery and the positive impact you bring to the world justified.
• If there were a book about your life, what would the readers be urging you to do right now?