Questions to ask yourself

From Answering these questions could change your life:

Could the act of answering open-ended questions about yourself give you new, important insights? It turns out the answer is “yes”. After running a series of five scientific studies, we’ve discovered a specific set of practical, yet rarely-asked questions that 83% of people reported were valuable for them to answer and that 78% said they would recommend to others. A remarkably high 88% of people even reported that they enjoyed answering these questions. We think you’ll be surprised at just how valuable answering these open-ended questions about yourself can be:

1. What in life gets you really excited?
2. What could you do to bring more of what really excites you into your life?
3. Summarized in just a few sentences, what is your life’s story?
4. What would you like the next chapter of this story to be?
5. What would you say is the greatest accomplishment of your life so far? Brag for a minute.
6. What do you want to make sure you do, achieve, or experience before you’re gone?
7. In recent years, what’s the biggest lesson you’ve learned about yourself?
8. Who inspires you most, and why do you find them inspiring?
9. What was the biggest turning point in your life, and how did that experience change you?
10. What are you taking for granted that you want to remember to be grateful for?
11. Think for a moment about the biggest problem right now in your life. If that problem was happening to a close friend instead of to you, what would you say to comfort or advise that friend?
12. What meaningful or important thing should you tell a particular person that you haven’t said to them yet?
13. When are you going to tell this person this meaningful or important thing?
14. What’s one of the best days you’ve had in your entire life? Describe what happened that day.
15. What in your life that you have the power to change is most limiting your long-term happiness?
16. What could you start doing now to address what you said is most limiting your happiness?
17. If you had to have roughly the same work day, 5 days a week, for the next 10 years, what activities would you ideally want this work day to consist of?
18. What can you do to make your current job closer to this ideal, or to help you get a job that is closer to this ideal?
19. What is the most important thing that you know you really should do but which you have trouble getting yourself to do?
20. What could you do now to make it more likely that you actually do this important thing?
21. What do you think is holding you back from achieving more in your life than you’ve achieved so far?
22. What could you start doing now that would help address what you said is holding you back in life?
23. In your opinion, what is the purpose or meaning of life?
24. How is the very best version of yourself different from the way you sometimes behave?
25. What has kept you hopeful in life’s most challenging moments?
26. During what period of your life were you the happiest, and why were you so happy then?
27. Imagine that you received a message from a version of yourself five years in the future. What warnings would the message give you, and what advice would it offer about how best to achieve your goals?
28. If you knew for a fact that you were going to die exactly 10 years from now, how would you change your current behavior?
29. Suppose you knew that you were going to die instantly (but painlessly) in exactly 7 days. What would you spend your last week doing?
30. If you could plan one nearly perfect (but still actually realistic) day for yourself, what would you spend that day doing? Describe that day, from when you wake up until you go to sleep.
31. When is the soonest that you can treat yourself to this perfect day, or to another day that you’ll really enjoy and remember?
32. What valuable things have you learned, or what useful takeaways have you gotten, from answering these questions?

Notes:
(i) Cf. Asking questions to build relationships. In this case, the relationship is with yourself…
(ii) I wonder nonetheless whether these are also great questions to ask other people.
(ii) These are great examples of questions which are open-ended, but not unmanageably big. See How to ask great questions.