I’m at the CMD-D conference in Santa Clara this morning. I’m actually a couple hours early because my body is still on Central time. So I figured I’d take a minute and answer the most common question that I got after my last appearance on Mac Power Users.

I mentioned (kind of in passing) that you can nest tags using punctuation, in my case a colon. Here’s an example:


So in my system, there’s also a #Context tag, in this case it would be #Work. (Context tags are the only tags I capitalize, and I don’t know why, but I’m consistent.) My auto-filer would take the file with the above tag, find the freelance folder inside of my base Work folder, and then file it under jappleseed/scripting. The way my system works, if there was a folder tagged @script even deeper within the @jappleseed folder, it would file it there instead of creating the folder at the base. So that’s why I started using these punctuation-split tags. There are some additional benefits, though.

Spotlight breaks the tag up on the punctuation when searching. This means that I can still search for tag:script and find all of my script files, regardless of the preceding portion of the tag. But I can also search tag:jappleseed:script and create an automatic boolean AND search, as if I’d searched tag:jappleseed AND tag:script. The file will also show up for the search tag:freelance and tag:freelance:jappleseed.

It also makes autocomplete work more efficiently for you. Once you’ve tagged a file with any freelance:jappleseed subtag, it will show up in autocomplete for you after just typing “free,” letting you tag the file with all three tags at once.

When I’m using these grouped tags, I start the tag with a colon as well: :freelance:jappleseed:script. It doesn’t affect Spotlight’s ability to search in any way, but helps keep my nested tags together in the list. This system doesn’t help with tag pollution (having too many tags), but that helps keep the lists neater. You can also do searches like “NOT tag::*” to exclude any tags starting with a colon. That also works with other punctuation, so in my system I can get a list of all project folders in a given context with tag:#Work AND tag:@*.

So basically you’re creating nested groups that are children of a particular tag. You can then have a smart folder for all of the “jappleseed” client files, and use Spotlight within that folder to find various tags. You can even set Finder to group by tags in the list, so it creates an automatic visual “folder” hierarchy for each smart folder.

It’s not a necessary tool. You could always just use all of those tags separately and run “AND” searches to combine them. I like the shortcut, though, and in combination with tag autocompletion, it makes filing quite easy.