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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? 
September 10, 2025 3 min read

The Freewrite 500 Writing Contest — Terms and Conditions

Last Updated: 10-09-2025

By submitting an entry to The Freewrite 500 Writing Contest (the “Contest”), you agree to abide by the following Terms and Conditions.

1. Organizer

The Contest is organized by Freewrite, a brand owned and operated by Astrohaus, Inc. (hereinafter referred to as “Freewrite”, “we”, “our”, or “us”).

2. Eligibility

  • The Contest is open to individuals who are 18 years of age or older at the time of entry.

  • Employees of Freewrite, the Flash Fiction Institute, and their immediate families are not eligible to enter.

  • Void where prohibited by law.

3. How to Enter

  • Entries must be submitted through the official entry form to be made available on Friday, September 22.

  • Entries must be original works of flash fiction no longer than 500 words.

  • Only one entry per person is allowed.

  • Entries must be written in English.

  • The deadline for submission is 11:59 p.m. EST on September 22, 2025. Late or incomplete entries will not be accepted.

4. Entry Requirements

  • Submissions must be the entrant’s own original work and must not have been previously published, including on personal blogs or social media.

  • Entries must not contain any material that is obscene, offensive, defamatory, or otherwise inappropriate.

  • By entering, you confirm that your submission does not infringe on any third-party rights, including copyright, trademark, or privacy rights.

5. Judging and Winner Selection

  • All eligible entries will be judged by a panel of reviewers affiliated with Freewrite and the Flash Fiction Institute.

  • Judging criteria include length, creativity, and adherence to theme, and overall quality of writing.

  • The winner will be notified via email.

6. Prize

  • The winning entry will be published on both the Freewrite Blog and the Flash Fiction Institute Blog.

  • The winner will receive recognition across Freewrite and Flash Fiction Institute's social media platforms.

  • No cash prizes will be offered. Prizes include a Freewrite Traveler, a Words Are Hard writing prompt deck, publication on the Freewrite blog and the Flash Fiction Institute blog, and a free flash gym session hosted by the Flash Fiction Institute.

7. Rights and Usage

  • By entering the contest, entrants grant Freewrite and the Flash Fiction Institute first publication rights. This means Freewrite and the Flash Fiction Institute have a non-exclusive, royalty-free, worldwide license to publish, reproduce, and distribute the submitted entry in connection with the promotion of the Contest, including on their websites, blogs, email newsletters, social media channels, and more.

  • After initial publication, all rights revert back to the author, who is then free to republish or distribute their work elsewhere. However, we request that any subsequent publication acknowledges Freewrite and the Flash Fiction Institute as the original place of publication.

  • The winning author will be credited by name or preferred pen name when their work is published.

8. Privacy

  • Personal information collected during the entry process will be used only for the administration of the Contest and in accordance with Freewrite’s Privacy Policy.

  • Entrants may be contacted by Freewrite regarding their submission or related opportunities.

9. Disqualification

Freewrite reserves the right to disqualify any entry that:

  • Violates these Terms and Conditions,

  • Is found to contain plagiarized material,

  • Is deemed offensive or inappropriate,

  • Is submitted by someone ineligible.

10. Limitation of Liability

Freewrite is not responsible for:

  • Lost, late, incomplete, or misdirected entries;

  • Technical failures of any kind;

  • Any injury or damage to persons or property related to participation in the Contest.

11. Governing Law

These Terms and Conditions shall be governed by and construed in accordance with the laws of the State of [Insert State], without regard to its conflict of laws principles.

12. Contact

For any questions regarding the Contest, please contact us at:
📧 hello@getfreewrite.com.

September 10, 2025 1 min read

One blank page. 500 words. Zero fear. Let’s see what happens when you stop thinking and just go. It's the Freewrite 500, presented in collaboration with the Flash Fiction Institute.

August 22, 2025 3 min read

Most of us are surrounded by screens all day. To get your writing done, take writer Shannon Liao's advice and unplug.