Migrating from Obsidian to Day One
Alright, I finally did it. I pumped all my Obsidian journal entries into Day One. Here’s the post (or one of them, anyway) that spurred me into action.
Obsidian is ideal on paper. Everything's in one place and stored as local, plain text files: my journal entries, my blog posts, my notes, my reference files, my music library, and so on. I love that, and I’ve been reluctant to break the consistency.
But I’m realizing that Obsidian just doesn’t spark much joy. Not for journaling, at least. This is why I dabbled with Apple’s Journal app a bit ago. Day One and Journal handle images and locations so much better than Obsidian can, and they make browsing through old entries a much easier and more pleasurable experience.
To be fair to Obsidian, this makes perfect sense; these apps are purpose built for journaling while Obsidian is a jack of all trades. And sure, Obsidian has plugins for everything under the sun. But I don’t like relying on plugins.
Beyond this, Day One has a bunch more features that appeal:
- If you add an image to an entry, it asks if you want to change the entry date to match the one in the image’s metadata. That’s so great for retroactively creating entries, which I find myself doing a lot because it’s so easy!
- On This Day feature.
- Web version of the app. This is especially handy since I’ve moved my personal notes off of my work laptop.
- Entry locations and a map view.
- Calendar view, which shows pictures for posts that have them. Love this.
- Polished UI that’s quite pleasant to write in.
- Great tagging support.
- Daily journaling prompts. I usually don’t like these but I like some of Day One’s prompts.
- You can email an entry to your journal. I expect that to come in handy. I use this feature a lot with Things, my task manager.
- Classy focus mode.
How I migrated
I used Day One’s JSON import and wrote a Python script to build the JSON and zip it up.
While there are a lot of fields in the example JSON file, I used only three: creationDate, text, and tags.
My Obsidian journal entries’ dates and titles are stored in the filenames, which look like this:
/path/to/journal/2025-10-30 On the flight home from Austin.md
I parsed them out in Python, using the date for creationDate and adding the title to the top of the text field with a Markdown heading.
Taking the above example, my text field looks like:
# On the flight home from Austin\n\n[rest of the entry's content goes here]
Day One parsed that just fine, turning my Markdown title into the Day One entry’s title. Nice.
I didn’t bother automating the image import.
Day One supports it, but it would’ve meant using regex to find all the image links in my Markdown, downloading those image files, assembling them in a Photos/ subfolder, and adding another field to my JSON so Day One can reference them.
Not rocket science, but a time investment.
Since I hadn’t used photos extensively in my old journals, I figured I’d do this part manually.
It might even be fun to have to go look at those old pics again.
(Or so I justified my laziness.)
I’m enjoying Day One so far and looking forward to journaling more often with it.
Cheers!