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💡 The Big Idea: File Automation Can Help Keep Your Notes Organized — But Only After You Decide How You Want to Group Things Together

People ask me all the time about how I organize my file folders in Obsidian.

The short answer? I don’t really worry about it.

In my opinion, creativity requires a little bit of chaos.

I don’t even really think about it until I’m working with a note, and it becomes obvious that I should group with other related notes.

That doesn’t mean my Obsidian vault is a complete mess. But it does mean every connection means something.

In this newsletter, I want to share the ways you can connect things in Obsidian, how I use them to group things together and share a workflow that helps keep things organized using file automation.

Keeping Things Organized

There are three main ways you can link things together in Obsidian:

1. Links — you can create internal links between your notes by using [[ around your note titles, which causes them to show up in the Outgoing Links, Backlinks, and Local Graph.
2. Tags — you can add tags to either a line or a note (by putting it in the metadata at the top). Clicking a tag in the Tag pane opens a search that shows all the tags in the left sidebar.
3. Folders — you can group related files together in folders (and sub-folders), then drill down into those folders using the File Explorer in the left sidebar.

But the truth is that how you use these tools can and should be determined by the way you work with your notes & ideas.

That’s why I’m not a big fan of prescriptive organizational systems like the PARA Method.

🔥 My hot take: By using someone else’s system, you’re stifling your creativity.

Creating is supposed to be a little bit messy. In his book, A System for Writing, author Bob Doto talks about the role of anarchy and chaos in the creative process.

That doesn’t mean you have no organizational structure whatsoever for your notes. But if things are a little bit messy, that’s ok.

The key is that whenever you group things together, they actually mean something.

This is how I separate things in my head:

• Folders are for grouping things together by type
• Tags are for grouping things together by topic
• Links are for creating intentional connections between ideas

But how this gets implemented is always changing and evolving.

That being said, I have landed on a few specific use cases for each. The one I want to talk about in this newsletter is based on folders and how you can use file management tools like Hazel to help keep things where they belong.

Auto-Archiving Files Based on Property Metadata

I use Obsidian for all of my writing projects.

I organize those writing projects in folders (i.e., Newsletters, Video Scripts, Articles, etc.) and manage them using the excellent Projects plugin. This plugin helps you track what you’re writing using different views (i.e. table, calendar, Kanban, etc.).

Using this plugin, I can track my projects in columns using a Kanban view that is built on the status of the writing project itself. For example, the status for this article is inprogress so Projects automatically lists it in the appropriate column:

What’s great about this plugin is that you can simply drag a note from one column to another, and the status property is automatically updated.

For example, if I drag this newsletter care to the published column, the status of the note instantly gets updated from status: inprogress to status: published.

And that’s where Hazel comes in.

With Hazel, you can create rules to watch specific folders. When something in that folder matches the rule, Hazel automatically takes the pre-determined action.

In this case, I have a simple rule that does two things:

• Watches for a plain text Markdown file that contains the text status: published
• Automatically moves that note into a sub-folder called Archive

That way, the Articles folder only contains notes for articles that I’m actively working on.

But this is just one example. There are lots of ways you can use Hazel to keep your Obsidian vault organized. Another use case I’ve seen is creating a date-based rule that moves all your old Daily Notes to an archive folder based on waiting a set period of time after the date they were created. Or you could simply apply a tag to a note in your Obsidian idea inbox and have it automatically sorted into the appropriate folder.

If you use folders at all to keep your Obsidian notes organized, then it’s definitely worth using an app like Hazel to create a few rules to help you keep things neat & tidy.

And if you’re looking for a PC equivalent (since Hazel is Mac only), I’ve heard a lot of good things about an app called File Juggler.

😎 Something Cool: Dynamic Outline Plugin

Yes, Obsidian already has a built-in outline core plugin, but it’s pretty basic and is often hidden in the sidebar. If you want something that’s a little more functional, the Dynamic Outline plugin is a great upgrade.

The main thing this plugin gives you is a floating table of contents that helps you navigate your longer notes more easily. There’s also a current section indicator to show your position in the note, a search bar you can use to quickly find and jump to headings, and keyboard shortcuts for navigating the outline.

If you want to give the standard Obsidian outline tool an upgrade, check out Dynamic Outline.

📚 Book Notes: The Courage to Be Disliked

Cory & I recently read The Courage to Be Disliked by Ichiro Kishimi & Fumitake Koga for Bookworm, and I enjoyed it more than I thought I would. It’s an interesting book about Adlerian psychology, told as a conversational fable between a young student and an older philosopher. The style reminded me a lot of the Patrick Lencioni business fables (i.e., The 5 Dysfunctions of a Team), but the topic is a lot more approachable.

If you want to download my mind map notes for this book, click here.

— Mike