I have been feeling frustrated with my personal organization of late. I had a bit of time before starting a new project, so I put some time into improving my process. The post below is a simplified version of the notes I took while I looked for alternatives. I’m sharing this as an example of how I do research, and as a more realistic example of the architectural report structure I typically use, which I’ve written about before.

According to my records, I spent 28 hours working on the decision. This breaks down to about 22 hours testing the eight finalists, 4 hours researching options, at a summary level, and 2 hours of planning. Of the time spent testing, I spent between 30 and 240 minutes each for 7 of the 8 finalists. I spent 8 hours testing Obsidian, though most of that was testing and improving the processes I ended up using.

I started this task thinking purely about about improving my working notes and personal task list, but as I dug further in, it became apparent that I could centralize many of the different organizational tools I use. That process is still under way as of this writing, but I must say, it feels pretty nice every time I delete another productivity app.

Purpose

This document is a decision record explaining my choice for replacing my organizational system. Theoretically, it is intended for myself as a way to guide my thinking, but in reality, I am only writing it out in this form to share on my blog. The real document I used as the first draft for this post is similar, but a lot rougher, and with other unimportant details jumbled in.

Some of this text is inserted purely as commentary for the blog post, and would not normally be included in a decision record document. I have marked such text with italics, this paragraph included.

Context

  • My personal backlog is spread across two email accounts, Trello, Remember The Milk, a few Evernote notes, and occasionally project management systems used by my customers. I would like to have one place where I can see all of my priorities so that I can easily find the next most important thing to work on, and to ensure important tasks don’t get dropped.
  • I am spending a fair bit of time fiddling with cards in Trello, trying to update them, reset them, and change the dates on them. I don’t feel like I ever have a good view of my priorities there. I am also worried that important tasks are getting dropped because of it’s limitations.
  • Remember The Milk is great for managing recurring tasks, but it doesn’t work for anything more complicated than simple chores. Some of my projects have a lot of research notes, open questions, and subtasks that are best kept all together. Trello can handle more complexity in a card, but I still find it limiting for a project that is more than a couple days of work.
  • Keeping a backlog spread between notes in Evernote and Trello lists causes unnecessary work reconciling the two. I also end up searching both when I want to find notes from something I’ve done in the past.

Decision

  • Try using Obsidian
    • Use a minimal number of vaults
    • Set up the Tasks plugin
    • Create a daily note template that includes incomplete tasks scheduled for that day and a view of my calendar
  • Migrate one type of information at a time. Migrate new types as I get more accustomed to Obsidian.

Options Evaluated

Finalists

I tested each of these applications before choosing Obsidian.

The table below is what I call a decision matrix. I put options across the top, and questions down the side. I don’t particularly like tables for this sort of data, but so far, they’re the best solution I’ve found. A nice feature of this format is that I can keep expanding the list of questions as I learn more about the available options and the problem I’m trying to solve.

I don’t go out of my way to answer every question for every option. When an option stacks up enough limitations or blockers, or I just have a feeling that it’s not what I’m looking for, I focus my attention on something else. The tabular format makes it easy to see when I’ve done this, but also makes it possible to pick up where I left off if all the other options prove to be worse.

I like to use background shading in the cells (green, yellow, and red) to mark answers that are notable strengths, weaknesses, or blockers. For the sake of this blog post, I’ve added emoji to the cells instead.

Obsidian Logseq Amplenote Tana Joplin Eidos Columns
Decision ✅
Powerful for note management. Tons of plugins. Healthy community. Local storage and markdown notes make it easy to extend or migrate away.

Not sure if it will be powerful enough for my chaotic brainstorming.
 ⚠️
Looks pretty powerful for brainstorming and task management. Might not be ideal for general notes, though. Probably not ideal for sharing with wife.		 Looks promising and very usable, but it doesn’t seem to be as promising as Obsidian.
Tasks and calendars are cool, but I don’t feel like they are as powerful.
Vendor lock-in is also a significant deterrant.		 ⛔
Very cool UI, great features, but there is vendor lock-in, and it’s not extensible.		 ⛔
Useability is too poor. I don’t think I could handle using it. My wife would find it worse.		 ⛔
Cool idea, but it doesn’t seem mature enough.		 ⛔
Useful way to manage lists, but not powerful enough for anything else.
Strengths Lots of plugins
A bit easier for my wife to use		 Great for storing knowledge and maybe brainstorming and task management Excellent for scheduling tasks. Included Meeting agent (though it’s not integrated with Zoho)
Inbox concept is cool
Smooth UI
Can attach notes to stuff in the calendar
Integrated AI		 Collaboration features Very Extensible Really good at lists
Drawbacks Switching between edit and view mode is annoying, but plugins might be able to help with this Would be difficult to share things with my wife
Harder to learn and use		 Todos are first-class, but don’t really fit into the notes. They’re more like reminders than artifacts.
Less powerful features with drawings and code. No executable code.		 Useability is pretty poor Weird activation key
Doesn’t seem finished yet		 ⛔
Not good at anything except checklists
Performance ✅
Really fast		 ⚠️
A bit sluggish, but might improve with database version.		 Seems pretty fast
Price Sync: $4/m/user USD
Commercial: $50/y USD (two or more employees)		 ✅
Free, Open Source		 ⚠️
Free Forever (which makes me nervous about longevity) Commercial: $6/m (+more sync)		 $90/yr Free / $80/yr Free, Open Source
Syncing Obsidian Sync is supposed to be good.
Other syncing solutions are available.		 Logseq Sync (Paid Feature) Or: sync files yourself or: store them in git! Naturally online. Naturally online. Do it yourself, or use their cloud. OneDrive supported also. Self-hosted API: https://github.com/mayneyao/eidos-api-agent-node Cloud-based
Test: Make a daily Plan with projects and chores Very powerful tasks plugin queries tasks from multiple notes. Takes a bit of work to set up. Can use todo items across any area of notes. Can then write queries to surface these in the daily journal. Really good at this. Can easy drop items into the calendar. Daily jots for notes and tasks. Buttons for bringing incomplete tasks over from previous day. Cannot view work and personal calendars together though. In the instructions they say that people don’t really want this… hrmm ✅
Can make anything a todo item, and it’s automatically put into appropriate lists.		 ⛔
Terrible ux		 Can build my own list… Easy
Test: Recreate Mule project notes ✅
Easily with hierarchal tasks, and notes, and anything else I want		 ✅
Hierarchy, namespaces, todo, with optional schedules. Fantastic!		 ⚠️
It’s easy to make pages, and to make tasks that are pages, and tasks that are nested… but it doesn’t feel like a first class thing.		 Fine ⚠️
Kind of like evernote, but worse experience		 ⛔
Too complicated

Has chat-style notes, but they’re too limiting
Handling Tasks ✅
With tasks plugin https://github.com/obsidian-tasks-group/obsidian-tasks		 ✅
Relatively easy with TODO. Has multiple statuses such as complete and cancelled		 Easy to add tasks to notes or other things Very easy to schedule tasks.

Tasks that are completed are removed from notes.		 Ctrl+Enter
Limited statuses
Can create multiple similar supertags with different fields		 It has some functionality, but it’s not pleasant to use Ctrl + Enter Easy, efficient
Handling Subtasks ✅
Very easy with nesting		 ✅
Very easy with nesting		 ⚠️
You can nest tasks, but they exist somewhat independently of their notes, and the relationships don’t get maintained. If you complete the parent, the children get completed.		 Easy Not capable natively Infinite hierarchy Only one level
Handling recurring tasks ✅
Yes		 ✅
Yes		 ✅
Yes. And easy to do.		 ⚠️
Nope, but there are workarounds		 ⛔
Supposed to be possible, but can’t figure it out		 ⛔
Can’t handle it
Handling drawings ✅
Excalidraw and Canvas pages.

Ink plugin looks interesting.		 ✅
Yes, and infinite canvas boards
/draw		 Excalidraw No Can draw freehand and use text. rearranging objects, but no built-in shapes. ⛔
pictures, not notes
Handling Code ✅
Yes. And it can run it too!		 Yes Yes Yes, but it seems a bit buggy. Yes, but the UI got buggy when it was added. Markdown code blocks are supported
Inline executable code? ✅
Math plugin
Any code I want with Execute Code plugin		 ✅
math, with variables and functions		 No No ⚠️
Yes. Math via plugins.		 Don’t think so
Handling Diagrams ✅
Canvas: Nice block-and-arrow diagrams Excalidraw and Mermaid support!		 ✅
Embedded mermaid!		 ⚠️
There’s a plugin, but it doesn’t work very well		 No Can embed mermaid drawings directly Nope
Test: Reading List It’s possible with dataview or folder table plugins, but it’ll take some work to set it up. Kanban board may work too. Should be fine Not good at lists Yes. With fields and sorting
Test: Development Recommendations Pretty easy, but may want to customize it a bit. ✅
Should be excellent		 Should be okay. Linking across content seems harder. Nope
Test: Brainstorming Should be fine. Canvas is cool for brainstorming. Easy to dump notes on board. ✅
Should be great for this		 No Nope
Test: Storing Receipts ⛔
It can do it, but with synching mechanism, they have to be downloaded to all devices that access them, even phones.		 ⛔
Probably not good at this		 No
Handles Tables Markdown tables. Some plugins to make editing them more tolerable. Not markup ones
Tabulation? obsidian-dataview plugin No Yes, with fields Nope
Grouping / sorting data Yes, via dataview plugin. Advanced queries are possible, but the syntax is a bit crazy looking. Some pretty powerful built-in queries Nope
Data Organization Vaults (separated), Folders, Files. Daily Journal Pages, Namespaces, Tags, Daily Journal Similar to Logseq Folders (recursive) Documents Lists
searching ✅
Embedded queries. Plugins for more advanced cases.		 Embedded queries. Language is bizarrely complicated. ✅
Built-in queries.
Links to other applications Supports links Supports links Yes
Integrate live data from other applications Not built in iframes with inline html No ✅
Markdown: Remote-Note-Pull
Scan from Rocketbook ⚠️
Not built in, but maybe possible with integrations		 Mail-to-note feature Not built in Email -> Note with Joplin Cloud
Mobile Usability ✅
Excellent		 Nice inbox for dumping things in.
Can access notes via web, but editing looks tedious
Can my wife use it? ⚠️
Obsidian Sync can be used for sharing a vault with multiple people. Can only share at the vault level, though.		 ⛔
Sharing between users is not officially supported. It would be hard for her to use.		 Probably. It supports sharing via tags She probably wouldn’t like it Too difficult to use
Automation / integration ✅
Plugin: Local REST Api
Local markdown files.		 ✅
It’s all just markdown files! Also an API		 There is an API API for Pro account Local API Local API for integrations
Client Type Installed app Application or Web Page PWA, or Installed App Web page Executable, Mobile Local Web App Can be self-hosted
License Proprietary AGPL-3.0 Proprietary Proprietary AGPL-3.0 AGPL-3.0
What is it written in? NA Clojure & TypeScript NA NA TypeScript & Rust TypeScript
Plugins? ✅
A lot of them!		 ✅
Yes. There are a LOT of them around.		 ⚠️
Yes, but doesn’t seem like a healthy ecosystem		 ⛔
Not supported		 Yes. Seems to be a healthy ecosystem.
Plugin languages supported? TypeScript, JavaScript TypeScript TypeScript
Where is data hosted Locally, wherever you want, or Cloud: USA Locally or wherever you want Their cloud Google Cloud Local or Numerous Cloud Options
Offline Mode Yes Yes ⛔
No		 Yes
Data Encryption ⚠️
None locally.
E2E encryption in their sync option.		 ⚠️
None locally. Transmit as you want.		 ⛔
“data is encrypted both at rest and in transit”		 E2E Encryption is possible, but not enabled by default.
Export capability ✅
Local storage is markdown. Lots of plugins for exporting.		 ✅
It’s just mardown files PDF Export
Slide generator		 JSON or Markdown JEX format (Joplin Export file) - meant for backup PDF
Markdown
Import from Evernote Supported https://help.obsidian.md/import/evernote ⛔
Not supported		 Supports ENEX files Links may not work where titles differ
Company Health Based in Oakville, Ontario Active Development Appears to be private, small company.

Obsidian Alternatives Evaluated

Obsidian was a bit different from most of the other options that made it to the finalist stage. Once it began to stand out as a frontrunner, I did a quick search for apps similar to Obsidian, and tested the following two as a result:

  • Amplenote - included in matrix above
  • Affine.pro - disqualified pretty quickly because there was no mobile option and had a very small library of plugins

Initial Scan for Options

The following were discovered and briefly researched to decide if they should be evaluated further.

I only evaluated these options on a few criteria that were easy to look up. This allowed me to narrow the field quickly, as opposed to testing each one in detail. I went in interested in network-style tools, and excited by the prospect of something open source, extensible, and based on a transparent data format.

Because of the limitations of tables, and because I usually have a lot more options that questions in this phase, I’ve swapped the table axes from my usual for a decision matrix.

Price Handling tasks Handling Subtasks Mixed Content Support Notes
✅
Tana		 $90/yr Okay ⚠️
Seems possible with tags, but complicated.		 ✅
Good		 Seems like a popular new thing. Powerful note features with fields and supertags.
✅
Columns		 It’s all lists Lots and lots of lists.
Routine Free ⛔
Lots of incomplete features
boostnote.io $8/user/month Maybe Can’t tell Code formatting. Diagrams. Links to other apps. ✅
Open source client
✅
Eidos		 ✅
Free. Open Source. Locally Hosted.

 Supports Extensions. Can execute code. Supports spreadsheets Locally hosted, offline. Has local API. Offline LLM support.
✅
Joplin		 Pro: $80/yr Free if you host your own data Can insert tasks Plugins. Rich Text and markdown support. Supports extensions. Code blocks. OCR!! Open data. You can store it yourself or use their cloud option. Seems like a better, free Evernote
Milanote $12/yr Tasks ⛔
Doesn’t appear to		 Notes. Todo lists. Photos in a visual canvas. Very visual. Good for brainstorming.
✅
Logseq		 ✅
Open Source.		 ✅
Tasks can be inter-mixed in notes. Use queries to access them later. Grouped by blocks too.		 ✅
Seems like it’s possible to build pages with piles of tasks embedded in them.		 Networked outliner. Use tags to link things together.
✅
Obsidian		 Sync $4/month ✅
Kanban plugins.		 ✅
Canvas. Supports plugins. Tasks. Indenting. Code blocks.		 ✅
A popular choice

Summary

It was a bit of a process to do the research, but I’m glad that I did. Moving all my organization systems has the potential to be time consuming. The greater the cost of making a mistake, the more up-front effort is justified. This also gave me an opportunity to explore various options and styles and get better informed on how I could organize everything.

Now that I’m a few weeks into the switch, I’m still loving Obsidian. I have a few more things to migrate, but generally it has been better than my expectation in every regard.