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?
💼 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?
