deariary vs Day One vs Notion vs Obsidian vs paper: which diary actually sticks?
We have used every journaling tool on this list. Not just evaluated. Used, loved, and eventually abandoned.
The pattern was always the same. We would discover a new tool, get excited about a specific feature, and think “this is the one that will make me actually keep a diary.” It never was. The feature was never the problem. The writing was the problem.
This post is the story of that cycle, and why we eventually built deariary to break it.
Day One: “this design will make me want to write”
Day One is gorgeous. Apple Design Award winner, over 150,000 five-star reviews, owned by Automattic. The timeline view is clean. The calendar shows your streaks. The fonts are perfect. Opening it feels like opening a leather-bound notebook.
We thought the beauty would pull us in. And it did, for a while. Day One auto-tags entries with weather, location, and step count, so each entry feels rich even before you type a word. The On This Day feature surfaces old entries and makes you glad you wrote them. You can add photos, videos, audio recordings, drawings with Apple Pencil. You can even print your journal as a hardcover book.
The app works on iPhone, iPad, Mac, Android, Apple Watch, Windows, and web. Instagram and Strava auto-import natively. Zapier / IFTTT connect Spotify, YouTube, Fitbit, and others. The Premium plan ($4.17/mo billed annually) adds unlimited devices, unlimited photos, and end-to-end encryption. The free tier gives you 1 device, 1 photo per entry, and 1 journal.
Day One is a great product. We mean that. But the streak died. The reminders became noise. The Today View showed us calendar events and photos as writing prompts, and we closed the app because turning prompts into paragraphs still felt like work.
The feature we thought would save us: beautiful design and rich media. What actually happened: we stopped opening the app.
| deariary | Day One | |
|---|---|---|
| Entry creation | Automatic, every morning | Manual (with templates and prompts) |
| Effort required | Zero | You write every entry |
| Platform | Web | iPhone, iPad, Mac, Android, Apple Watch, Windows, Web |
| Data source | Your connected services | Your memory (with auto-tags for weather, location) |
| Media | Text | Photos, video, audio, drawings |
| Automation | Native integrations | Instagram, Strava native; Zapier / IFTTT for others (Premium) |
| Encryption | Server-side | End-to-end (Premium) |
| Free tier | Up to 1 integration | 1 device, 1 photo/entry, 1 journal |
| Paid | From Basic plan | $4.17/mo billed annually |
Notion: “this template will keep me organized”
After Day One, we moved to Notion. The idea was that structure would solve the problem. We built a journaling database with date properties, mood selectors, energy levels, gratitude fields, and a “highlight of the day” column. It looked incredible.
For about three weeks.
The template itself became a project. One more property. One more view. A linked database for weekly reviews. A formula to calculate journaling consistency. We spent more time tweaking the system than writing in it. And when we sat down at 11pm and saw seven empty fields, it felt like homework.
Notion is a powerful workspace. The Free plan gives individuals unlimited pages and blocks. It supports offline on desktop and mobile. But it has no journaling features: no streaks, no reminders, no flashbacks, no auto-tagging for weather or location. If you want external data flowing in, you need Zapier or Make, which cost extra and require their own configuration.
The feature we thought would save us: total flexibility to design the perfect template. What actually happened: designing the template became the hobby. Writing in it did not.
| deariary | Notion | |
|---|---|---|
| Setup | Connect services, done | Design template, configure properties |
| Entry creation | Automatic | Manual |
| Purpose | Diary | Everything (diary is a side use) |
| Integrations | Native (GitHub, Calendar, Slack, etc.) | Zapier / Make (extra cost and setup) |
| Learning curve | Minimal | Moderate to high |
| Offline | No | Yes (desktop and mobile apps) |
| Free tier | Up to 1 integration | Unlimited pages for individuals |
| Paid | From Basic plan | From ¥1,650/mo per member (Plus) |
Obsidian: “this plugin setup will automate everything”
Next we tried Obsidian. Local-first, Markdown-based, free, with over 2,000 community plugins. The Daily Notes core plugin creates a fresh note for each day. Add Templater, Dataview, and the Calendar plugin, and you get a journaling system that feels like you built it yourself. Because you did.
We loved that our diary was a folder of .md files on our own machine. No cloud dependency, no terms of service, no account. We could read our entries with any text editor. We set up templates with YAML frontmatter, Dataview queries for monthly summaries, and a calendar sidebar showing which days had entries.
Setting that up took an entire weekend. It was fun. And then we had to actually write in it every day.
We missed a Tuesday. Then a Thursday. Then a whole week. The calendar sidebar showed the gaps. No plugin could fill them retroactively, because the raw experiences were gone. If you want to sync across devices, you need Obsidian Sync ($4/mo billed annually, $5/mo monthly) or a DIY solution with iCloud or Syncthing.
The feature we thought would save us: a custom-built system with total data ownership. What actually happened: the system was perfect. We did not use it.
| deariary | Obsidian | |
|---|---|---|
| Entry creation | Automatic | Manual (template-assisted) |
| Data storage | Cloud | Local Markdown files |
| Data ownership | Exportable | You own the files completely |
| Plugin ecosystem | Built-in integrations | 2,000+ community plugins |
| Sync across devices | Yes (web) | Obsidian Sync ($4/mo) or DIY |
| Backfill missed days | Yes (data still exists in connected services) | No |
| Cost | Free tier available | App is free; Sync is paid |
Paper: “the simplicity will remove all friction”
After three digital tools failed, we went analog. A Hobonichi Techo. ¥2,200, one page per day, no notifications, no plugins, no pricing tiers. Just a pen and a page.
Writing by hand felt different. Slower, more intentional. The first two weeks were the best journaling we had ever done. Short entries, but real ones.
Then the busy days came. The pages stayed blank. We carried the notebook everywhere but opened it nowhere. There is no search, no backup. If you lose it, everything is gone.
The feature we thought would save us: the tactile simplicity of pen on paper. What actually happened: busy days produced blank pages, then guilt, then more blank pages.
| deariary | Paper | |
|---|---|---|
| Entry creation | Automatic | Manual |
| Searchable | Yes | No |
| Backup | Cloud (automatic) | None |
| Privacy | Server-side security | Physical possession |
| Tactile experience | None | High |
| Cost | Free tier available | ¥500 to ¥3,000 per notebook |
The pattern
Every tool followed the same arc:
- Discovery: “this feature will make journaling work for me.”
- Honeymoon: two to four weeks of consistent entries.
- Friction: a busy day, a tired evening, a missed entry.
- Guilt: the streak breaks. The blank page stares back.
- Abandonment: we stop opening the app. The notebook goes into a drawer.
After going through this cycle with Day One, Notion, Obsidian, and paper, we realized the problem was not the features. Every tool on this list is good at what it does. Day One is the best multimedia journal. Notion is the most flexible workspace. Obsidian gives you the most data ownership. Paper gives you the most intentional writing experience.
None of them solved the actual problem: we did not write on the days we were busy, tired, or not in the mood. And those are most days.
Why we built deariary
deariary does not ask you to write. It connects to the services you already use every day (GitHub, Google Calendar, Slack, Todoist, and others) and generates a diary entry from your activity. When you wake up, your yesterday is already there.
This is a fundamentally different bet. Day One, Notion, Obsidian, and paper are writing tools. They give you a place to write and hope you show up. deariary is a recording tool. It captures what already happened.
The diary exists whether you participate or not. No streaks to maintain. No templates to fill. No blank pages.
This means deariary is not for everyone. If the act of writing is your practice, if you journal as meditation, deariary will feel wrong. Use Day One. Use paper. Those are genuinely good choices for people who can sustain the habit.
But if you have tried all of these tools and your diary still has more gaps than entries, the problem is not the tool. The problem is that every tool requires you to write. deariary is the only one that does not.
