88 Prompts You’ll Want to Show Your Grandkids Someday

If you’ve followed along with Write Your Wellness for some time, you know that this blog has destroyed a few journals with expressive art and self care projects. But not everyone wants to get rid of their journals forever. In fact, a few of you only keep journals so you can show your grandkids what life was like for you.

There is something beautiful about writing a journal that outlasts you. This is exactly why I have teamed up with the American Diary Project to talk about how to keep a journal if you plan on keeping it forever. This week, you can find my article on how to make your journal interesting to archivists HERE.

In the meantime, this post covers something a little different. Your journal’s audience won’t always be archivists and scholars. More likely than not, the people who will cherish your old journals most are your kids, grandkids, and so on. These are prompts for them.

“When I Was Your Age…”

A grandparent classic. If you want to show your grandkids these journal pages, you absolutely need to hit them with the “when I was your age”. These journal prompts will help you do just that.

1.        In broad terms, describe your childhood.

2.        How did you survive Middle School?

3.        How did you survive High School?

4.        What did you do when you had your first crush?

5.        Did you match your parent’s parenting style? Why or why not?

6.        What childhood memory literally haunts you to this day?

7.        What is the very, very first thing you remember?

8.        When did you learn the value of a dollar?

9.        What do you wish you knew earlier in life?

10.   What is a trend from your childhood that you just don’t understand anymore? What does if feel like to see something that was once “cool” go out of fashion?

11.   What did you like most about childhood?

12.   How did you choose what to do post High School? Did you wish you chose differently?

13.   When did you know you wanted children of your own?

14.   What was the hardest part of your life so far?

15.   What was the easiest part of your life so far?

16.   What were you into most as a kid, teen, young adult, and adult? How did your tastes change?

A Little Slice of Life

You never know what about your current life will seem wild to future generations. That’s why it is good to throw in a couple of “mundane” journal pages. These prompts might sound boring but they make a reader feel connected to the real you.

17.   What does a typical Monday look like for you?

18.   How do you do your weekly errands?

19.   What is your least favorite chore?

20.   Name something that you thought would be cool forever…until it wasn’t.

21.   How were you successful today?

22.   Why have you set up your routine the way that you have?

23.   What is most stressful on the News right now? How has it affected you?

24.   Write out a playlist of all you most-listened-to songs. Why do you love them?

25.   Try to explain the latest social media trend. Good luck.

26.   How do you drink your coffee/ tea/ etc.?

27.   Who do you see most often day-to-day? What are they like?

28.   Describe your neighborhood in detail. Those businesses and homes might not be there in 30, 50, 100 years.

29.   What’s a gadget that you’ve recently bought that actually improved your life?

30.   Where do you feel most comfortable outside of your own home?

Reveal *THAT* Family Secret

You don’t need to share everything in-person. Some dramas are best discovered while flipping through a journal. A word of warning, be mindful that you intend to show your grandkids this journal. Only be as detailed as *they* need. If you want to go deeper, consider a different kind of journal.

31.   Have you had to cut ties with anyone before? What led up to that hard decision?

32.   Is there anything that shocked YOU to learn about older generations? How did that change your perspective on things?

33.   When have you felt the most guilt and shame?

34.   If you could, who would you like to apologize to?

35.   Have you ever been misunderstood in a situation? What is your side of the story?

36.   What is the secret you will take to your grave (but it’s fine if people know after)?

37.   Be honest, when have you been the drama? Do you regret it?

38.   What have you been reluctant to share with people lately? Why?

39.   What is your deepest regret?

40.   Have you ever been “cancelled” by someone? How did you survive it?

41.   When have you cheated the system? How do you feel about that?

42.   What are the family cycles that you hope to end forever?

43.   How is each side of your family different? Why do you think that is?

44.   Who is the oldest ancestor you know about? What do you know about them?

Life Lessons That Matter

What mark do you want to leave on the world? For many, it is very important to show your grandkids some life lessons. These prompts get at the root of your values and insights about life.

45.   What is something you think your culture gets wrong about life?

46.   How do you prioritize your time? Why is this significant?

47.   Name one life lesson your parents tried to teach you. Do you agree with it?

48.   What matters most to you? Should everyone prioritize life this way? Why?

49.   If people only remember you for one thing, what would it be

50.   What did you have to learn the hard way?

51.   Name something in life you think is really overrated? What should people focus on instead?

52.   How do you think people should show up for family (literal or found family)?

53.   When have your values been tested? How did you decide what to do?

54.   Who is someone that has inspired your values?

55.   What type of people should you seek out in life? Who should you avoid?

56.   How is your adult life different from what you expected as a kid?

57.   Have you ever had a change of heart? How did that happen?

58.   What values have always been important to you?

59.   Where can you find the answers to most of life’s questions?

How I Met Your Other Grandparent

Believe it or not, you don’t need 9 seasons to explain how you met your partner. In fact, you only need a few journal prompts. Choose the prompts that make the most sense to you and your love story. Future generations will absolutely eat this up. I guarantee it.

60.   Write your love story from a third person point of view.

61.   What drew you to your partner initially?

62.   How has your partner changed the way you view love?

63.   Where did you go on your first date? How did it go?

64.   When did you realize that your partner was “the one”?

65.   What about your partner continues to amaze you?

66.   What about your current relationship do you wish for your future children?

67.   How has your relationship changed you?

68.   What was your first fight as a couple? How did you repair?

69.   What is one lesson about love you wish everybody knew?

70.   Name something about your partner that no one else knows about.

71.   What was your wedding like?

72.   Do you have any little traditions with your partner?

73.   How is your partner’s family different from yours? How did you deal with this?

74.   What about your partner do you wish carries through future generations?

Add a Little Humor

It is an absolutely fact that everybody loves a sassy old person. You might not be old yet, but the people who read this journal will likely know you when you’re older. Give ‘em the razzle dazzle by throwing in a couple of wild stories and (gasp) swear words. Laughter is essential when you want to show your grandkids your life.

75.   What is the craziest adventure you’ve ever been on?

76.   Do you have any petty grudges? Spill the tea.

77.   What’s the juiciest gossip you’ve heard this week?

78.   How did you know it was time to “grow the F*** up?”

79.   When have you really let loose?

80.   Write about a time you *really* got in trouble as a kid.

81.   When was your most embarrassing moment? Why was it so mortifying?

82.   Name a time when you may or may not have been the bad guy.

83.   Do you have a go-to party story? Write about it!

84.   What’s something you got away with (but shouldn’t have)?

85.   Who were you during your single life before meeting your partner?

86.   What is your favorite joke?

87.   Who has changed the most in your life? What were they like before?

88.   What is something that surprises most people about you?