
The days are getting shorter, and we’re entering the “dark half” of the year – The autumn equinox is on September 22. This is the perfect time for a little introspection to prepare your whole life to hunker down for the rain, snow, & cold (if that’s the weather you get where you are)!
In this post, I’d like to share some journaling prompts to help you contemplate where you’re at and where you’d like to be over the coming months. Prepare for a combination of practical planning and emotional unpacking.
Why Journaling Matters This Time of Year
This time of year invites inward focus because there usually aren’t as many events available to steal your outward attention (concerts, carnivals, etc).
It’s always better to spend some time with yourself than it is to scroll social media or binge watch comfort shows on TV.
Journaling gives you a mirror for your inner world — and during darker months, that mirror becomes even more valuable.
The Prompts
✨ Emotional Unpacking
- What needs to be unpacked, mentally & emotionally, over the coming months? Now is the time of year to lean in to the shadows to find true light.
- What fears, resentments, or regrets surface more clearly in the quiet/dark? How can you hold space for them without judgment?
- What outer (public facing) parts of your life could be put to rest for the winter?
- What inner areas of yourself could use some fresh attention?
🏡 Home + Environment
- Tidy up outside if winter is coming, and then start cleaning inside.
- Brainstorm tasks & organize by area / room.
- Bust out the cozy blankets & hot cocoa mugs! And if you don’t keep your Xmas lights up year-round…consider it? I do! 😜
🎃 Holidays + Traditions
- What are your plans for the holidays?
- Do you need a Halloween costume?
- What might you be doing for Thanksgiving, Xmas, New Year’s, Festivus, whatever you celebrate?
- Do you need to get anybody gifts?
- Don’t forget what’s important to you — How do you envision each of these holidays going, ideally? What intentions do you have for each (such as more peace, less spending, reconnecting with tradition, creating new rituals)?
📅 Planning for the Year Ahead
- Do you need to plan for a new planner for next year? Don’t overcomplicate it! Better to undercomplicate it & add as you find necessary. Sometimes all you need is a monthly or weekly calendar!
🎯 Goals + Reflection
- How are your goals going?
- What can you still accomplish by the end of the year?
- What’s worth dropping or postponing so you enter the new year lighter?
- What’s something surprising you’ve accomplished so far this year that wasn’t on your original list?
- Wins: What fun did you have this past spring / summer? What did you accomplish? Little things still count! What did you overcome? What are you proud of?
- What am I looking forward to most in the coming months?
Closing Thoughts
This time of year isn’t just about survival — it’s a chance to deepen, let go, and realign. Try at least one of the prompts above, or spread them out over the coming weeks, and see what comes up for you.
Save this list to revisit throughout the season — you might be surprised how your answers shift over time.
Which of these prompts speaks to you most right now? Drop it in the comments or share it with a friend who journals.
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Rock on!

