20 Questions to Capture a Life Worth Remembering
🧒 Childhood & Family
1. What is your earliest memory?
Prompts:
Where were you?
What sounds, smells, or feelings stand out?
Were you alone or with someone?
2. What was your home like growing up?
Prompts:
Was it quiet or lively?
Did you share a room?
What did it smell like when dinner was cooking?
3. Who had the biggest influence on you as a child—and why?
Prompts:
Was it a parent, grandparent, teacher, or friend?
What did they teach you or model for you?
4. Did your family have any traditions or sayings you still think about?
Prompts:
Holidays? Birthdays? Weekly routines?
Any funny or meaningful phrases your parents used?
5. What’s one lesson you learned early in life that’s still true today?
Prompts:
Did you learn it through success or failure?
Who helped you learn it?
🧑 Adolescence & Becoming Independent
6. What was school like for you? Any teachers you’ll never forget?
Prompts:
Were you shy, social, curious?
What subject excited or intimidated you?
7. When did you first feel like an adult—or want to be one?
Prompts:
Was there a moment you had to grow up quickly?
Did you feel prepared?
8. Did you ever rebel or take a big risk in your teenage years?
Prompts:
What rules did you break—or want to?
What happened because of it?
9. What music, fashion, or trends defined your youth?
Prompts:
What did your clothes say about you?
What music did you play on repeat?
10. What did you dream your future would look like back then?
Prompts:
Did you imagine a career, family, lifestyle?
How did reality compare to that dream?
❤️ Love, Family, and Milestones
11. How did you meet your spouse or first love? What drew you to them?
Prompts:
Where did you meet?
What was your first impression?
12. What was one of the happiest moments of your life?
Prompts:
What made it unforgettable?
Who was there with you?
13. What was one of the hardest decisions you ever had to make?
Prompts:
What was at stake?
How did you make peace with your choice?
14. How did becoming a parent (or mentor) change you?
Prompts:
What surprised you about yourself?
What moment made you feel most proud?
15. What advice would you give someone just starting a family today?
Prompts:
What mattered most in your journey?
What do you wish someone had told you?
đź’Ľ Work, Purpose, and Challenges
16. What did you do for work, and what did you love (or dislike) about it?
Prompts:
How did you choose that path?
Was it fulfilling—or just necessary?
17. Did you ever feel like you found your purpose? If so, when?
Prompts:
What gave you a deep sense of meaning?
Did your purpose change over time?
18. Was there a moment you almost gave up—but didn’t? What kept you going?
Prompts:
What obstacle were you facing?
Who or what helped you push through?
19. What’s something you’re proud of that most people might not know?
Prompts:
Did you accomplish it quietly?
Why is it meaningful to you?
🌟 Wisdom, Legacy, and Reflection
20. If you could leave one message or story behind for future generations, what would it be—and why?
Prompts:
What do you hope your grandchildren or great-grandchildren remember?
Is there a story you want passed down?
