After giving Day One’s Gold Tier an honest chance for about three months, I’m returning with my journal to Obsidian. While the annual subscription is fine overall, there are several major issues that make Day One unusable for me compared to Obsidian.
Here is why I’m switching back:
- Halfway AI Implementation in Day One. I find the presence of AI in a journal absolutely essential (though it must remain purely optional, as it is in Day One). However, the current implementation in Day One is totally absurd. The 🤖 is sandboxed; it can’t see regular timeline entries. This is an insurmountable obstacle for me because I need "play-by-play interaction" from morning to evening. If you’re going to implement AI, please make the robot fully available so we can interact with it/him/her directly within regular timeline entries.
- Atrocious Block Editor. The block editor in Day One is extremely buggy and constantly freezes (or at the very least annoyingly wobbles) across the Windows app, the web app, Android, and iOS. We already know from WordPress how atrocious the Gutenberg block editor is; using this version is outright torture. It’s incredibly frustrating compared to the absolutely smooth, lightning-fast, and equally (or more!) capable pure Markdown editor in Obsidian. I know Automattic now owns Day One and will likely insist on using this block editor, but to me, it’s a serious design mistake.
- Terrible Feature Parity. In Obsidian, you get every single feature on all platforms where applicable. If a feature makes sense on mobile, it’s there on both platforms. In Day One, you get certain buttons on iOS, different buttons on Android, and still other buttons on Windows and the web. The iOS version of Day One is clearly the most advanced, while all other platforms lag behind. This inconsistency is deeply annoying.
- Difficult Export Options. There’s no easy, user-friendly way to export your entries from Day One. The only option to get a user-friendly Markdown export is on iOS (and presumably macOS), but the Android Markdown export is buggy and provides fewer options. From Android, Windows, and the web, you’re typically stuck with nothing but the technical JSON export, which isn’t user-friendly at all.
I’ve now purchased the $140 annual subscription for Obsidian Copilot, the finest AI integration plugin in Obsidian. Fortunately, it has nothing to do with Microsoft, so it’s great.
You can integrate any AI model using the Obsidian Copilot plugin, including completely free local LLMs if you can install them on your machine, but also using the standard API tokens route. There's also the middle ground between the two: that $140/year subscription I've just purchased, which provides you with a robot derived from Google's Gemini Flash 2.5. That's not a great model by any means, but it's comparable in performance to the ChatGPT model (4o-mini, 4.1 and other older models) that Day One has now integrated. Crucially, though, in Obsidian, thanks to its 100% transparency, you can tweak that internal robot's performance to your liking using any number of custom prompts. This is plain impossible in closed software like Day One.
While Obsidian Copilot can be used fully for free, I chose that subscription so that I can use a faster and slightly more advanced online robot. (Yeah, if I were paranoid, I could use my local robots, and then my journal would remain 100% private and would even work fully offline, despite AI integration.)
But because I also use Obsidian Sync, my journal automatically syncs across all platforms. I can talk to my journal assistant on every tablet, mobile phone, and Windows computer. It works flawlessly and 100% transparently. The Markdown files are just wonderful.
The finest feature of Obsidian Copilot is that when you talk to the 🤖 in your journal, a Markdown backup of that dialogue gets automatically created in the background. Whenever you say something or the 🤖 replies, that most recent response is automatically appended to that Markdown backup file and synced across all your devices, even during an ongoing conversation. It’s truly a live dialogue that helps you maintain your journal.
I’m really disappointed that Day One chose not to offer this kind of live dialogue, restricting it instead to that isolated sandbox of Daily Chat. That’s simply not enough.