100 + prompts to get you started
What lesson in life did you learn the hard way?
Describe a time when your life took an unpredictable turn.
Who do you think of when you imagine someone saying, “I believe in you.” Now, write about a time in your life when just knowing someone believed in you made a difference.
Write about a friend from each major stage of your life, and let us know why you think of that person as your friend.
What slice of your life would you like your children to know that shed light on what has meant the most to you?
What do you wish you could have asked your parents?
What message would you like to send to your Mother? Your Father?
As you look back over your life what threads do you recognize?
So far, what are your sacred moments that come to mind?
Write about several moments in your life that touched your deepest feelings.
What one thing did you save that belonged to your parents? As you look at it, what do you think? What are your feelings when you touch it?
Write about a time when you went through a spiritual crisis.
Write about some places of beauty that touched your heart and that you cherish even to this day.
What is the most surprising gift you ever received? Explain the circumstances around receiving this gift.
What is the most enjoyable gift you gave to someone else? Explain.
Write of several qualities of your grandparents that you would most like your grandchildren to possess.
Write about the greatest peer pressure you felt as a teen since your grandkids feel it every day.
Write about the hardest phone call you ever made. Write about the hardest letter you ever wrote. How about the hardest received?
Write about the worst rejection you experienced as a teenager. How did you handle the situation?
Write about how your family handled the bad times during your early years: divorce, death, arguments, lawsuits, and/or estrangements.
Were there any cautionary tales within your family when you were growing up? Write about one.
Write of one specific time when you felt hopeless and alone. What helped you through the experience? As you write, think of how best your grandchildren can learn from this experience.
When you were a kid who could you always go to for honest answers? Explain who, explain why.
Write of a single experience out of your past that found you caring and supportive of someone who was going through difficult times.
Write of an instance when time seemed to stop and you knew you were part of a moment that held great significance.
Write how you would choose to die plus the timing. Explain why.
Explain to your children some of the things you want to experience before you die. Write a list. Explain why.
Share your feelings about being left alone should your spouse die first.
What apprehensions do you have about suffering? How will you explain these feelings to your grandchildren?
Write about a time when you struggled with your identity and self-worth. This may be helpful to a grandchild.
Do you believe there is life in the universe beyond planet Earth?
What is your faith and how do you experience it?
List five things you like about yourself and write a 50-word paragraph on each.
Write about something you learned from forgiveness.
Write about something you learned from fear.
Write about something you learned from contentment.
Write about something you learned from discipline.
Write about something you learned from joy.
Write about an experience in your life when you and your family experienced a flood, fire, or natural disaster. Describe it.
Write about an early drought that impacted you and your family.
Describe a dust storm you experienced as a kid. What was it like?
Describe the coldest and harshest winter you can remember.
What kind of heat did your house have when you were growing up? How did you keep warm? What was the process of staying warm in dead winter as a kid?
What was the biggest snowstorm or blizzard you remember as a kid? What things did you have to do to survive such a storm?
Were people more secure in their family values when you were growing up than they are now? Why? Why not?
How common were working mothers in your day? Have working mothers been good or bad for our society? Explain why or why not.
Write about a time in your childhood when your father knew best.
Write about a time when your mother knew least.
What was the balance between freedom and authority in your home when you were young? Write an experience from both.
Write about a time when you and your new spouse/significant other had an experience that was wild and spontaneous.
Make a list for your grandchildren of some things you currently consider romantic.
Describe a getaway experience you and your spouse/significant other had that was memorable.
Write about an early experience when you and your spouse/significant other were aggressive and extravagant in your romance.
Write about an experience where your romance was so predictable and boring that it was humorous.
Where did you live during your childhood days and who lived with you?
What kinds of make-believe do you remember playing as a child?
Name and describe the pets you had when you were in grade school. Write about them.
What do you remember feeling on the first day of school? Describe it.
What do you see going on around you at mealtime when you were a child?
Write a memory of the kind of music you typically heard as a child.
Write a memory of the kind of music you typically heard as a teenager. Did you buy it? Dance to it?
Do you listen to music as an adult?
What fills up your senses?
What is your favorite meal and why?
What do you love to look at?
What thrills your taste buds?
What scents entice you? Why? What scents repulse you? Why?
Describe the cars you have owned in your lifetime.
Write about a memorable fishing trip.
Write about a memorable camping trip.
Write about a memorable vacation.
If you were baptized, what were the circumstances around the event?
What were the circumstances around your baptism?
Did you have a memorable babysitting experience when you were a teenager? Explain.
Write of one significant Depression experience that has stayed in your memory all these years.
Write a memory of your first few days in Navy boot camp, or Army basic training.
Write about some of the ways you carry a positive influence from your parents. List them and explain each. Write of some ways you carry a negative influence.
Write of an experience out of your past that found you in a very deep and powerful relationship with your parents.
Write of an experience out of your past that found you in a very deep and powerful relationship with your children.
Write of an experience out of your past that found you in a very deep and powerful relationship with your grandparents.
Write of a childhood experience of genuine solitude you had that impacted your life? Explain the circumstances and what you learned.
Write about your most romantic experience(s) ever.
What roles did you have as (choose one): an only child; as the oldest child; as the middle child; as the youngest child.
Describe the house your family lived in the first years of your life.
Describe all the nicknames of your siblings and friends and the history behind them.
Write about your weirdest Christmas Eve.
List some of your favorite things and explain why they are your favorites.
What is/was your profession?
What was the worst thing that ever happened to you at work?
Who is the one person I really miss in my life during the holidays? Why?
Write about one childhood Christmas that really stands out? Why?
Write what the word “blessed” or “lucky” means to you? Why?
In your family or group of friends… Who’s the Most …
Social
Who’s the Best Cook
Who’s the Most into Politics
Who’s the Funniest
Who’s the Most Creative
Who’s the Wildest
Who’s the Most Reclusive
Who’s the Most Generous
Who’s the Best Storyteller
Who’s the Most Traveled
Who’s the Best Organized
Of those elections that you remember, what do you remember most about each?
Which election was the first that you participated in (actually voted)?
What are your current political views and have they changed over the years?
Describe your teenage hangout.
Describe the view from a particular window.
Describe a sport you play or played.
What is your all-consuming hobby?
Are you a sports nut? How so? What teams?
What makes you crazy—pet peeves? How do you handle them?
City-born or country-bred?
Describe a favorite teacher or business mentor.
What is your sense of humor like? Your favorite joke? Were you the class clown?
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