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September Journal Prompts. Fall Into a F*ckin’ Breakthrough!

With a few minutes of curiosity, what can we find out? These daily September journal prompts ask you to risk new insights onto the page.

See if you can answer the questions honestly. It’s okay to change your mind. Figure out what you really think.

I suggest giving yourself at least ten minutes or one full page per prompt, but go as long as you like!

If we haven’t met, I’m Megan. I’m a trained facilitator, respectful writing coach, and award-winning author. I journal daily-ish. I do it because it’s fun, because the privacy of it feels like freedom from expectations, and because I think it helps me be more honest and confident in my writing and in my life. If you’d like to try something new in your journaling this month, here’s my Megged-up list of September journal prompts.

September Journal Prompts

Click here for a printable .pdf file of all 30 September journal prompts.

1. How do I like to learn things?
2. What might I find in wide open space?
3. Who do I respect, and how can I show that?
4. What expectations have I already outgrown?
5. What phrases or sayings or slang have I picked up from specific people, and when, and why?
6. What genre am I in?
7. When have I laughed so hard I lost control?
8. What do I think crying is for?
9. What have I been meaning to get around to, and what’s in the way of me getting it done?
10. What am I in the process of growing towards?
11. If I had five million dollars but had to donate it all to a single cause, where would I give and why?
12. What advice would I give past me from a year ago?
13. What’s important to me today?
14. When I meet someone new, what things do I notice first?
15. What’s the story of my name?

(psst… if you want mood music to help you focus, here’s my personal journaling playlist:

ok, back to the prompts…)

16. What tattoo might belong on me (which isn’t already there)?
17. What qualities do I have that are useful in tough situations?
18. What would I do differently if I knew I’d live forever?
19. What happens if I try to list one event or experience or milestone from each year of my life so far?
20. What are some useful next steps to take, and which will I do first?
21. Who challenges me in a good way?
22. What belongs to me?
23. How do I like to fall asleep?
24. What seeds have I planted that might still be growing?
25. How can I use my strengths to help people?
26. What am I glad I’ve never done, seen, or learned?
27. Why don’t I quit everything and start over?
28. What would I do for a million dollars cash?
29. How many places, people, things, and experiences can I list that I honestly and truly love?
30. What’s my idea of a just reward?

Those are my September journal prompts. Thanks for checking them out.

Journaling doesn’t have to lead to more, but it can. Sometimes our biggest and best ideas pop out when we’re just trying to be honest with ourselves. If you recognize the truth on the page… I hope you’ll follow it and see where it takes you. That one sentence that feels alive, that spark of a joke or insight, or even that feeling you got while writing… do you want to take it farther? Could it be the start of an essay, a substack post, a keynote?

If you want to make an impact with your words, 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.


Writing coach Megan Cohen is a white cis woman with soft femme hair. She wears a black tee shirt and stands against a white wall. She smiles gently with warm eyes. Her skin is amazing even though she's middle-aged.

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)



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