Lately I’ve been thinking about making another run at file tagging. It’s kind of funny how these tech issues percolate up. It all started with some receipts that I wanted to save to both client folders and tax folders. I found myself creating duplicates to have them in two places at once, which rubs me, someone who used to save computer data onto a cassette tape, as fundamentally wrong.

Tags would solve that problem. I could barf tags all over the file and then find it easily enough later with any index. Spotlight is good for this. Houdahspot is even better.

Then I had another problem with a backlog of unfiled documents. I’ve got Hazle trained to auto-sort a lot of documents that come my way but between my various careers I also get a lot of oddball one-timer documents that don’t really lend themselves to Hazel rule creation. However, if tagged, Hazel could easily land those documents in the various big bucket folders in my system.

So I’m looking at a hybrid tagging system that will still work with folders at some level but also rely on tags to help sort, store, and find files. There still are a lot of downsides to tagging. It takes extra time and it has very shaky support on iOS. I’m making a list of problems as I go.

I’m only a few days into this new experiment so I’m not going to share results until I dive deeper but I will say early results are promissing. I’ll report back on this next month.