Late at night while reading the daily mass readings for the next day and thinking about how one can better understand oneself, I started writing. This list of strategic thinking questions emerged.

Strategic thinking questions aren’t only for businesses and organizations. Individuals can also strategic thinking questions to more thoroughly explore what’s important, where they are headed, and how consistently their actions support their goals.

26 Strategic Thinking Questions to Truly Understand Yourself


If you want to go exploring about yourself, pick a few questions and see where they lead you, and how your answers might cause you to change the path you are on right now.

  1. Who did you want to be when you were growing up, and who do you want to be now?
  2. What's going on in your life that is making a difference?
  3. Where would you spend every waking minute if you could?
  4. What are the EVERY day parts of your life?
  5. Who would you rather spend time with than anyone else in the world?
  6. What authority do you turn to first when there's a question?
  7. What's the most important thing to you in the world?
  8. What are you most unwilling to give up?
  9. Who would someone watching what you do and how you spend your time think your best friend is?
  10. Who would someone watching what you do and how you spend your time think is most important to you?
  11. What's the best decision you ever made?
  12. Who is the most important model for your behavior?
  13. Who wants to teach you something that you continually resist learning?
  14. What voice always grabs your attention, even amid the noise of everyday life?
  15. What brings the biggest smile to your face?
  16. When was the last time you cried your eyes out?
  17. When was the last time you laughed your ass off?
  18. What do you preach about to others, but typically fail to do yourself?
  19. What's the last important thing to you that you gave up on without accomplishing it?
  20. What ALWAYS makes you quit?
  21. What happened the last time you were so quiet and listened so hard that you were able to hear the huge message you needed to hear?
  22. Who REALLY knows you best, and do they know that?
  23. What person have you lost touch with that you most want to try to find to reconnect?
  24. Everything just fell apart - who you gonna call?
  25. What's the last thing on your mind?
  26. What will it be like on the dawn of your last great day?

Mike Brown

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