I’ve tried journaling in a dozen formats over the years, and none of them quite worked, not because journaling itself was the problem, but because most journals don’t talk back. In this episode I walk through how I used AI to turn a great, generic Notion journal system into something that actually thinks like me, and what that process taught me about the difference between a journal that helps you record your life and one that helps you understand it.
The problem wasn’t the journal, it was that the prompts weren’t me. I’ve been using a well-built Notion journaling template (Better Creating’s Life OS) for a while, and it’s genuinely excellent. But a lot of the built-in self-improvement prompts just didn’t match how my brain actually works, so instead of abandoning the system, I used AI to rebuild the parts that didn’t fit.
I built new templates around how I actually think, not how a template assumes people think. Field Notes for outdoor adventures, Thinking Out Loud for getting rattling ideas out of my head, Crossroads for weighing decisions and asking what’s actually irreversible, and my favorite, the Squirrel Hole, for tracking when curiosity derails my whole day and whether it was worth it.
Odyssey Planning became a way to check in on the future lives I’m considering — what my life looks like if content creation works out, what it looks like if it doesn’t, what it looks like if I keep the weight off versus if I don’t. Instead of picking one future and forgetting about it, I built in a regular check-in against all of them.
AI didn’t write the journal, it helped me articulate what I actually wanted to ask myself. The habits I track aren’t the standard gratitude-and-exercise list — they’re specific to what actually derails me, like whether I went to bed on time. And now the whole system, which I’ve started calling my Northwoods Almanac, can summarize patterns across a week, a month, or a year and hand them back to me.
The point of all this isn’t AI replacing reflection, it’s AI helping me ask better questions of myself. A blank page doesn’t ask you anything back. This does.
If you’ve tried AI journaling or you’re stuck trying to build your own version of this, I’d love to hear about it — leave a comment or send me an email.
Jill’s Links
https://jillfromthenorthwoods.com/ - Find my podcasts, videos, downloads and ways to contact me
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Email the podcast at [email protected]
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