23 Extremely Useful Questions

  1. Okay, it’s bad. What’s good about it?
  2. If it doesn’t work out, how long would it take you to get back to where you are now?
  3. What are ten ways you can improve it?
  4. Why are you doing that with your life?
  5. Did you choose this? Why? Why not?
  6. Is there a better way?
  7. Is your action based on short-term gratification or long-term fulfilment?
  8. What are the real-life, actual consequences?
  9. What would it look like if you were completely wrong?
  10. How can you ensure that if it fails, you still win?
  11. Is it worth it? Why? Why not?
  12. What would you have to do differently to achieve your five year goals in only six months?
  13. Are the people you spend the most time with helping or hindering?
  14. Who should you spend more time with / call more? Why don’t you already?
  15. Who should you spend less time with?
  16. What are your strengths? What are your weaknesses?
  17. What habits do you need to work on daily to compound exponential growth?
  18. Are you operating out of sunk-cost fallacy?
  19. Should you stick or quit?
  20. Who’s opinions matter to you? Why do they matter? What do they think about it?
  21. What do you want more of in life? What can you give up so that you have time and space for it?
  22. What are the biggest wastes of time and energy in your life? How can you get rid of them or drastically reduce them?
  23. Think about when you were the most happy in your life, why was that? How can you replicate that now?