Hello friends,
August was a pretty brutal month for me if I’m being completely honest. I spent the entire first week moving and unpacking, which is always stressful in and of itself. Then, my dogs immediately both got sick, which required lots of extra monitoring and bandwidth (plus it makes me sad to see them like that). At the tail end of their stomach bugs, one of my dogs had a spay appointment, which broke my heart all over again. She’s been in the cone of shame for almost 2 weeks now. And to tie this pity party all together, financially, it was an expensive month—all spent on things that were zero percent fun. It was also a very slow revenue month, considering most of my time and energy was spent on the move and my dogs. Needless to say, I fell out of many of my sacred routines, and for the first time in a long time, my life felt like it was being ruled by my nervous system again.
But! These things happen. Such is life.
It’s strange to think about the ways in which we all suffer from the human condition. Life constantly happening to us regardless of how ready we are to receive what it has to offer. And yet, somehow, we always tend to find our way through it. For me, September has always felt like a subtle turning point. The edges of summer begin to fray as the days become shorter. It’s like the universe is handing us a quiet invitation to reset. Something about the start of Fall just makes reflection feel sharper. It asks us what we’re ready to carry into the next season and what needs to be dropped like the leaves outside our windows.
That’s the spirit I wanted to bring into these prompts, because I know I’m not the only one on the cusp of a new season—literally and metaphorically. Since there are 30 days in September, I chose 30 prompts—one for each day, if you’d like. They’re not assignments or rigid tasks, just invitations. You can use them daily, or dip in whenever you want to press pause and reorient. I like to spend 5 minutes each morning journaling, but there’s no wrong way to approach these. The point is simply to create space for self-contact.
a quick note on journaling—
For me, journaling isn’t about keeping a record or writing beautifully. It’s about contact. It’s a way of pressing pause long enough to actually hear myself beneath the static and noise. When I put things on paper, the chaos of thought becomes something I can see and move around. Patterns emerge. The same fears repeat. The same desires keep resurfacing. And suddenly, what felt overwhelming becomes information I can actually work with.
What you write in your journal doesn’t have to be deep or poetic. Half the time mine is just bullet points, phrases, scattered observations, or crazy stream of consciousness. But even the messy fragments are enough, because the act of showing up regularly sharpens the signal. It creates a kind of mirror, one that doesn’t lie back to me or soften the edges.
This is what inspired me to build THE DAILY 5 framework—not as a rigid method, but as a way to keep myself honest. Just 5 honest minutes a day, repeated over time. It’s less about “journaling” in the aesthetic sense and more about tracking the undercurrent of my life. What always amazes me is how much clarity comes from the accumulation. Little notes that felt irrelevant in the moment reveal patterns once you zoom out.
Whether you use these 30 prompts as a one-off reset or you want to build a longer practice, the point is the same: to make space for your own mind. To listen closely enough that you stop moving around on autopilot. And to remember that the smallest act of attention—sitting down, opening the page, writing a single honest sentence—can shift the entire direction of a season.
30 prompts for September:
Week 1 — Grounding
What’s one thing you need to release this season?
Write about the thing you want most this season but are afraid to name.
Write about a time you found clarity in a period of transition.
What’s a truth you’ve been avoiding, even as it quietly changes shape in the background?
If this month was a chapter, what would its title be?
Where do you feel most grounded—physically, emotionally, spiritually?
Write a letter to the person you were five years ago.
Week 2 — Shedding
8. Which part of your life feels “overripe,” ready to fall away on its own?
9. What habit drains your energy more than you admit?
10. What’s a pattern you’re ready to compost into something more useful?
11. Which metaphor best describes your current season of becoming?
12. Which losses have secretly cleared the ground for something better?
13. Write about a time you chose to step into uncertainty instead of clinging to comfort.
14. What subtle ways are you betraying yourself right now?
Week 3 — Turning Inward
When was the last time you felt fully present with the natural world?
16. What part of you feels like it’s been lying dormant, waiting for a new season to wake it up?
17. What questions are whispering in your life right now, asking to be heard?
18. What memory keeps resurfacing like an uninvited guest, and what might it want from you?
19. Which fears feel louder than they deserve—and what smaller truths are they covering?
20. What rituals keep you tethered when everything feels in flux?
21. What’s the hardest question you hope no one ever asks you?
Week 4 — Looking Forward
22. What would your future self thank you for doing today?
23. If you could give the next three months a theme, what would it be?
24. Which parts of your daily life already feel aligned with who you’re becoming?
25. Where do you feel most at home in your body—and where do you feel exiled?
26. If you had to build your life around one principle only, what would it be?
27. What part of yourself feels like it’s just beginning to emerge?
28. What small risk could you take this month that might change the course of things?
29. What version of you are you quietly building with your daily choices?
30. Write a letter to next year’s self.
I hope you’re enjoying your long weekend. See you in September! 🍂
XO, STEPF
Looking for more journaling ideas?
Prompts for building a journaling foundation
Prompts for exploring your own contradictions
Prompts for identifying relationship patterns
Prompts for personal system building
MORE TO EXPLORE 🐆
Omg these journaling prompts are next level
I also moved and started law school this month. So much change at once can be welcome but it also forces reevaluation. Saved these prompts to visit through my month of journaling, thank you.