I'm a digital hoarder. I have a problem throwing away old files. For instance, last week, I found a bad photo from 12 years ago. Why have I kept it? At this point, it's probably because it's from 12 years ago.

And they aren't all in one place, either - I've got shit spread haphazardly between an old OneDrive, Notion, Apple Notes, Raindrop, USB sticks lying around, the "Documents" folder I keep forgetting exists, etc etc.

IRL, I'm a clean freak. On stressful days, I'll run around tidying rather than whatever I'm supposed to be doing. (Hello ADHD, my old frenemy.) This has not extended to my digital life. This spring (while it's still spring) I'm embarking on an effort to clean all this up. Digital Spring Cleaning.

Because a total cleanup is a massive undertaking, and I know I'll choke on yet another unfinished project if I bite off more than I can chew, I'm focusing this project solely on plain-text media for now. (If I'm game for another round of this afterward, I'll tackle my photos and reference image collection.) For my organization system, I've chosen Obsidian.

Obsidian is an incredible rabbit hole, if you let it be. There's a whole sect of YouTube of people sharing ways of getting Obsidian to do all manner of tricks. (And a lot of people shilling their own Knowledge Organization Methods™, Productivity Boosting Ecosystems™®️, and Life Management Systems™®️©)

Purposefully, I've not consulted YouTube, or any podcasts, or anything before starting this journey. Browsing the community plugins alone has a way of making one feel small in the face of a massive task like this. I started with default, out-of-the-box Obsidian.

Step One: Get everything in there

Added plugin: Importer.

Importer is an official plugin of theirs, which lets you pull in notes and files from loads of other systems. I started by importing my Apple Notes, which was mostly seamless. There were some files that failed the process, resulting in empty files. Thankfully there were about 10-20 of these files, so I could manually copy/paste those ones in to fill the gaps. I love the fact that it brought copies of all the image files and attachments too!

The files from Apple Notes all went into a folder that I blatantly labelled IMPORT so I know it needs organization still. The attachments/images all went into _bin automatically. I'm unsure at this point how I want to manage those, so for now, I put the attachments into their own subfolder for later: _bin/Apple Notes.

Next up was importing everything from Notion. I got my zip file downloaded from Notion, plugged it into the Importer, and hit Go. It went about as smooth as Apple Notes went, but with its own hiccups. Firstly, the attachments got dumped into the root folder instead of _bin, and they seemed to behave weirdly - as if the file navigation sidebar could show 15-20 items and no more, no matter how large the window is. I moved what I could see into _bin/Notion, and others would appear in their place. After a while, they all ended up in the right folder, though. Now that they're there, the sidebar is behaving again, and I'm thinking that might be a slight bug related to a lot of attachments in the root folder? Not sure.

These two imports were the large bulk of my text file mess. There's other items that would work super well in Obsidian that I will also move over, but I need to work out what I'm doing in here beforehand.¹

Step Two: Clean up, clean up, everybody everywhere

This is where I'm at now. The hard part. The reason people keep trying to sell me on different systems of taking and organizing notes.

I'll be sifting through the files in here, moving them to a unified folder structure that makes sense, and tagging them. Yeah, I've never tagged my notes before. This is as good a time as any to start, I suppose. I'll also be keeping an eye out for opportunities to link the notes together, since that's kinda Obsidian's thing.

Step Three: Using the thing

I'm drafting this post in Obsidian at the moment, even while the rest of it languishes in a big IMPORT folder. The editor is quirky, but it's one of the better Markdown editors I've used. I picked the Minimal theme, and its corresponding Minimal Theme Settings plugin.

In writing this one post, I've found these plugins super helpful:

• Templater: I now have a magic "New Blog Draft" button separate from the general New Note button.
• Write Good: Something that calls me out for using words like "just," "especially," and "only."²
• Better Word Count: Nicer settings than the default, what can I say?

This is going to be a process. I was originally going to write about the whole experience in one go, but I can already feel ideas slipping away. On top of that, the accountability of doing this more or less publicly will help me to put it above other temptations pulling at my brain.