Remember that childhood game of 20 questions? Well, it turns out that asking questions is still a great way to explore a subject in depth. It combines curiosity with some structure, and helps highlight what you know, and what you need to find out.

In that spirit, here are 20 questions about your future, relevant no matter how old you are today…

  1. How would you describe your general health?
  2. How “well” do you feel, in body, mind and spirit?
  3. Could you become healthier? What could you do to sort out or manage any health issues?
  4. How happy are you with your retirement savings and financial plan? What is ‘enough’ for you and will you have this amount?
  5. How satisfied are you with life in general?
  6. What would you like to do to increase your overall life satisfaction?
  7. Do you think your next decade(s) will be a continuation of your life right now, or will there be changes? In what way?
  8. Where does your sense of meaning come from now? How aligned are you with your values?
  9. How will you create meaning for yourself in your next decade(s)?
  10. How do you connect with your community? Where does your sense of engagement come from?
  11. What gives you a reason to get out of bed?
  12. How important are non-work activities (relaxation, hobbies, interests, leisure) for you now? In your next decade(s)?
  13. What feeds your soul?
  14. Have you got an unfulfilled dream or passion that you’d love to activate in some way?
  15. How happy are you in your relationships? Partner, friends, family, others?
  16. What are your likely responsibilities over the next 5-10 years – caring for children, parents, grandchildren or partner? Will this involve time, focus, support, money?
  17. Are there any conversations you need to have about the future? These could be with loved ones, professional advisers, people with whom you have any unfinished business…
  18. Who else needs to be involved in your planning/ Who is part of your day-to-day life and focus?
  19. Does your age define you, or do you define your age?
  20. Does your current identity define you, or do you define your current identity?
Joanna Maxwell


Signup to have my occasional newsletters delivered to your inbox