These daily May journal prompts welcome change and growth.
Digging up all that truth and creating new possibilities for yourself can be tough. A spoonful of sugar helps. That’s why in this month’s prompts, I’m balancing real challenges with gentle (and unexpected) delights.
In the words of the great Susan Sontag: “In the journal I do not just express myself more openly than I could do to any person; I create myself.”
If we haven’t met, I’m Megan. I’m a trained facilitator, respectful writing coach, and award-winning author. I journal daily-ish. It makes me a better writer and a kinder person. If you’d like to join me this month, here’s my Megged-up list of May journal prompts.
I suggest giving yourself at least ten minutes or one full page per prompt, but go as long as you like!
May Journal Prompts
Click here for a printable .pdf file of all 31 May journal prompts.
1. What does this feel like the right time for?
2. How many different kinds of plants have I seen this year?
3. What’s my relationship to forgiveness?
4. Which communities in my life do I want to step deeper into? Where might I want to back off?
5. If I were going to live forever, how would I spend tomorrow?
6. What are my beliefs about luck?
7. If I keep making my current choices, where might I be in six months? What about ten years?
8. What do I think money even is, for real, like, what IS money?
9. Whose blessing would give me peace? Why them?
10. Is there anything only I might know?
11. What’s my favorite thing about how time works?
12. When in life have I felt powered-up and in my zone?
13. What would be a better way to think about the year besides “four seasons?”
14. What’s a nice gift I’ve received from someone? How vividly can I recall the memory of getting it?
15. If everything on this page was going to come true exactly, what would I write?
(psst… if you want mood music to help you focus, here’s my personal journaling playlist:
ok, back to the prompts…)
16. Who do I think is a “good person” and why?
17. What have I gotten more skillful at in the last few years?
18. What part of my body works the hardest?
19. If today so far were completely wiped from my memory, what would I lose?
20. If I were forced to pick one person to allow to read this journal, who would I share it with?
21. What lies have I told (or wanted to tell) about my life?
22. What are my top three fruits to eat and why?
23. How would I approach an extra-terrestrial creature?
24. If ten thousand people were cheering me on, what would I want them to chant?
25. Who have I been a good influence on?
26. What do I think are some of the least important things in the world?
27. What skills am I using to overcome current obstacles?
28. What places feel restful to me?
29. What takes a lot of effort but feels worthwhile?
30. Who do I want to remember today?
31. What thrills me when I see, hear, notice, or find it?
Those are my May journal prompts. Thanks for giving them a look.
If you enjoy keeping a journal, that’s worth making time for… but it can also lead to something bigger. Getting real with your words in private is good practice for anything else you want to write. Make truth a habit. Start by thinking freely in your journal, build your strength and courage, and then (when you’re ready to level up) unleash your words on the rest of us.
If you want to go beyond the privacy of your journal and make a bigger impact with your writing, I’m available to give you f*ckin’ friendly, majorly honest sliding-scale creative writing coaching. Get your ideas into the world.
xo, megan
Or just go home to the blog.

These (hopefully) really quite helpful creative writing tips offer what I’ve learned as an award-winning author who writes a million words a year, and what I’ve learned about supporting others as a private writing coach.
There’s no one way to write. There’s only your way. I hope some of my tactics and ideas can help you find it.
Yup, I’m a writing coach.
I work with folks at all levels of experience and all levels of income. My writers range from unhoused teens living on the streets to C-suite executives who want to up-level their communication. If you want a private coaching session but can’t afford it, email megan@howtowritesomething.com and ask for scholarship info.
curious/confused?: what does a writing coach do (and not do)
THANK YOU to this month’s generously supportive patrons who are helping me build a digital library of free writing resources to support writers with different access needs! Three cheers for A.J., Dan, Jason, Jennifer, Jessica, Josh, Katherine, Kathleen, Marianna, Nell, Sarah, and some anonymous folks who’ve asked not to be named. Come on in, the Patreon’s fine.