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30 Prompts to Start Writing Your Memoir

May 05, 2023 | 2 min read
Woman writing memoir

Everyone has a story to tell. Here at Freewrite, our passion is helping people overcome the obstacles to writing and get words on the page.

Many #FreewriteFam community members use their Freewrite for journaling or to write memoir. But sometimes your own story is the hardest to tell. Where do you start? What’s interesting enough to include?

Our advice: Stop thinking; start writing.

And if you need a little help with the “start” part, here are 30 prompts to get you going. Pick a prompt, set a timer for 15 minutes, and WRITE ON!

  1. Describe yourself as a child.
  2. How did you get your name?
  3. Describe your childhood home. How did it smell? What was the temperature?
  4. Pick a number from 1-20. Write about your life at that age.
  5. What was your favorite book or movie as a child? Why? Do you still like it?
  6. When you were young, what did you want to be when you grew up? How close did you come to pursuing that?
  7. Describe someone you admired when you were young. Did your impression of that person change when you grew up?
  8. Tell the story of the best meal you’ve ever had.
  9. What do you remember (if anything) about your parents’ relationship? Either with each other, or with others?
  10. Do you have any siblings? If so, did you get along?
  11. Describe a hobby you used to have that you no longer do. Why did you stop?
  12. Describe the best day of your life.
  13. What was your worst fear at age 5? Age 15? Age 25? Now?
  14. Describe the very first trip you took away from your hometown.
  15. Write about a historical event that you lived through.
  16. Do you believe in the afterlife? Why or why not?
  17. What was your first job? Did you like it? How long did it last?
  18. How do you define loss? Tell about a time you experienced loss, in any form.
  19. Do you remember your first love? Describe them.
  20. Have you experienced a life-or-death situation? How did you feel?
  21. Tell the story of a moment when you were scared to do something but did it anyway.
  22. What’s more important to you: honesty or loyalty?
  23. At what moment in your life did you feel most loved?
  24. What has been the biggest challenge of your life thus far?
  25. Do you prefer winter, spring, summer, or fall? Why?
  26. Name one insecurity you have about yourself. Now tell a story about where that insecurity was born, or how it has affected your life.
  27. Do you believe people are inherently “good”?
  28. Name one thing you believed as a young person that you changed your mind about.
  29. What are you good at? Be honest and don't sell yourself short.
  30. What is your most prized possession? 
July 08, 2026 2 min read

We're about to hit 1 billion words written on Freewrite devices. And we're doing a giveaway to celebrate.

One billion words is an entire library! About 11,000 novels.

That's 920 full read-throughs of the entire Harry Potter series.

Roughly 23 complete sets of Encyclopedia Britannica.

And we're almost there. Want to be part of the journey?

One writer who participates in the journey to a billion will be chosen to receive a prize pack the likes of which we've never given away before. And you don't have to own a Freewrite to enter.

One lucky winner will receive a prize package valued at $1,595:

  • A Freewrite Ernest Hemingway Edition Smart Typewriter with case and polishing cloth ($1,099 value)
  • An Author Clock ($209 value)
  • A Freewrite Circa Leather Discbound Notebook ($159.50 value)
  • A free 1-year subscription to Freewrite Plus ($40 value)
  • A Brown Freewrite Embossed Deskmat ($59 value)
  • A Words Are Hard writing prompt deck ($29 value)

 

How do you enter? Write. That's it.

Specifically: 

👉 Write on your Freewrite and sync to Postbox.

👉 If you don't own a Freewrite, write in our free app, Sprinter, and sync to a Postbox account. (Directions to create a Postbox account can be found here.)

Every day that you log words in Postbox (which is automatically done when you write and sync in the Freewrite ecosystem) will earn you 1 entry in the giveaway of all giveaways.

The more days you write, the more entires you'll have when we hit a billion.

Time Is Ticking

Keep an eye on the counter on our homepage. When it hits a billion, we'll pick the winner.

Good luck!

The Freewrite Team

 

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