The 50 Most Important Questions to Ask Your Aging Parents This Year

These are the questions that matter most. Not the practical ones — not the location of documents or the passwords to accounts — but the ones that will still matter in fifty years, when the people you love are gone and your children are asking you the same questions you never asked your parents.

Ask one at a time. Record the answers. Let them talk for as long as they want. The pauses are as important as the words.

Childhood & Origins: 1. Where were you born, and what was it like? 2. What do you remember about your earliest childhood home? 3. What were your parents like? What do you most want me to know about them? 4. What was your family's financial situation when you were growing up? 5. What did your family do that made you feel most loved? 6. Who was your best friend as a child? 7. What were you afraid of? 8. What did you want to be when you grew up? 9. What is the earliest memory you have? 10. What was the best year of your childhood?

Young Adulthood: 11. How did you meet Mom/Dad? Tell me the whole story. 12. What were you like at my age? 13. What was the hardest decision you ever made? 14. What did you want that you never had? 15. What was the best year of your adult life? 16. What do you wish you had done differently in your twenties? 17. What were you most proud of before we were born? 18. What was your biggest failure, and what did it teach you? 19. Was there a moment when everything changed for you? 20. What did love feel like when it was new?

Values & Beliefs: 21. What do you believe in more than anything? 22. Has your faith changed over your life? How? 23. What is the most important thing you've learned about money? 24. What does success mean to you — and has it changed? 25. What do you think happens after we die? 26. What is the most important thing a person can do with their life? 27. What do you think you were put on earth for? 28. What makes you most angry about the world? 29. What gives you the most hope? 30. What do you know now that you wish you'd known at 30?

Family & Legacy: 31. What do you most want us to know about our family history? 32. Is there a secret in this family that I should know? 33. What do you hope your grandchildren inherit from you — not money, but qualities? 34. What do you want said about you when you're gone? 35. What are you most proud of in our family? 36. Is there anything you wish you'd said to me that you haven't? 37. What do you love most about our family? 38. What was the hardest thing about being a parent? 39. Was there a moment when you were most proud of me? 40. What do you want your legacy to be?

The Present & Future: 41. What brings you the most joy right now? 42. What are you still hoping for? 43. Is there anything you're afraid of? 44. What do you wish people understood about being your age? 45. What do you want your last years to look like? 46. Is there anything you've never forgiven yourself for? 47. Who in your life has most shaped who you are? 48. If you could say one thing to your younger self, what would it be? 49. What do you want me to make sure I never forget? 50. Is there anything you want to tell me that I haven't asked about?

Start tonight. With one. The rest can wait until next time — but not indefinitely.