I’ve recently written about note taking and de-cluttering with Yojimbo. The common theme through both of these posts was organization of digital “stuff”. Both posts touched on how tagging has changed the way I store and find this “stuff”.

Tagging in Expected Places

Tagging has become ubiquitous on blogs and web sites that rely on user generated content such as Flickr, YouTube and StackOverflow to name a few. Tags make searches more reliable and targeted browsing easier. Tagging allows items to fall into multiple buckets, so loosely related data can be brought together in a meaningful way. Tag clouds also provide a visual indicator of how much data on one topic is available related to another. A quick glance at a tag cloud on a blog can quickly show us the primary focus of the author. Tags make it easier to sort through and navigate vast collections of data, so it would be a pity to keep this functionality limited to the web and a small handful of applications.

Applying Tagging to the File System

Spotlight search is great for quickly finding files, but sometimes a file’s name and contents aren’t enough. Tagging files on the file system can provide the same flexible categorization of data that is available on many popular web sites. To make this work, we need to look at the technology for applying tags to your files and the available tools to take advantage of this new metadata once it has been applied.

The applications and techniques I’m focusing on here rely on the openmeta standard for adding metadata to files. Openmeta is an OS X specific technology, so this won’t directly apply to Windows users (but I have linked to some Windows specific information further down the page).

File Tagging Applications

There is a nice write up of file tagging applications on the App Storm site. I am going to talk about two of them here. Tagit and Tags.

Tagit

Tagit allows you to add tags by dropping files into the application. It also includes a search interface, but as I’ll explain in the next section, this isn’t really necessary once you have your files tagged. Tagit is a free application which is always nice, but it does mean you need to go to each file (or group of files) and drag it into the application to apply tags to your files.

Tags

Tags provides the same openmeta functionality as Tagit, but it is more fully integrated into the OS, allowing you to tag files in place in finder and in associated applications such as Mail and iPhoto. Tags makes the act of tagging your files as they are created much simpler. You get what you pay for here, and will pay almost $30 for the added convenience. You can download a trial from the Web site, so you can decide if it’s really worth it to you.

Making File System Tags Work For You

Making this work requires a few things. First off, you need to actually tag your files and stay in the habit. Like any system, it will only work if it is actually applied. Getting started will require some work up-front to go through and tag your existing files. Then there is the matter of keeping up with it as you create new files. If you use Tagit you will need to drag your files into the application, so it might be a bit more difficult to develop the habit and come up with a workflow that is right for you. If you are using Tags, it becomes a little easier sine this can be done in place or by dropping files into the application. I am currently running a trial of Tags and was able to apply tags to this file right in place. You should also know that since both Tags and Tagit use openmeta for tagging files, they can be used together. For example, I can drag a group of files into Tagit and add common tags and they are immediately available when viewing the tags for an individual file with Tags.

The next thing to keep in mind is while tags are very flexible, they can get out of hand. Try to avoid one-off tags. Anything that will probably only be applied to a single item, probably won’t be all that beneficial. Also avoid multiple versions of the same tag. If you write a lot of letters, use a tag like “letter” for all of them as opposed to “letters” for some, “correspondence” for others and the singular “letter” on the rest. If they are consistent, the system will work better for you. That being said, if you’re like me, synonyms can be handy so you don’t have to remember which word you used so using “letter” and “correspondence” together on all letters will work. For example, I like to use “manual”, “documentation” and “user_guide” together on documents that could be referred to with any of those names. Using a consistent tag for items related to a project, on top of tags that describe that specific item will help you find things that much faster. The most useful tags should describe the content and context of a file. Obviously these are my preferences and you will need to figure out what ultimately works the best for you.

Once you have your files tagged, now you need to put those tags to work. For me, this happens in a couple ways.

Search

With your files tagged, Spotlight can take advantage of these by explicitly using them in a search. By typing a tag name into spotlight, your tagged items will be included in your search results, but the tag will not take priority over other searched items such as document name and file content. To perform a more targeted search you can specify that you are looking for tagged items by typing something like tag: blog into spotlight. Now the results will return documents that have been tagged with blog and ignore items without the tag.

Tags also includes its own search that can be used in place of Spotlight and includes tagged items in searches without the tag: prefix. It also includes typical Spotlight results. This search also does a much better job of finding appropriate results when you type multiple tags into the search… Spotlight seems to be lacking a bit when you try to use multiple tags in your search¹. If you decide to pay the money for Tags, you might as well put the new search tool to use.

Smart Folders

Smart folders are basically folders that contain referenced items returned through supplied search criteria. You can setup smart folders to use tags as criteria, so files that may be spread across the OS in different locations can all be pulled together dynamically in a single finder window. Setting up a smart folder for your tags is pretty straight forward.

1. Select File -> New Smart Folder from Finder’s menu
2. Select This Mac from the “search criteria” bar in the window that appears
3. Click the “plus” button on the right edge of the “search criteria” bar
4. Click the “Kind…” pop-up button and select Other…
5. Select the Tags attribute from the dialog sheet that appears. Checking this will add it to the menu for next time.
6. Select matches from the second pop-up button on the right side of “Tags”
7. Type in the tags you want into the text box on the right
8. Click Save.
9. Check out the results.

Now the contents of your folder will dynamically update with new files, from anywhere in your directory structure, tagged with matching criteria, and if you remove a tag from a file or group of files, they will no longer show up in your smart folder.

Conclusion

I still have files neatly arranged in folders and I don’t ever foresee abandoning the hierarchy of folders for storage. Tagging files has allowed me to rely on search combined with smart folders to find exactly what I’m looking for without having to think about where I keep things stored. I lean towards search most often so I don’t need to use the mouse and anytime I can remove the mouse from the equation, I consider it a step in the right direction.

Unfortunately, as I mentioned earlier, openmeta is only available for OS X, but this Lifehacker article on tagging and saved search in Windows Vista may be helpful if you are a Windows user interested in doing this. I still use Windows XP at work, but hopefully I’ll be able to employ this once we are upgraded to Windows 7.

I should also mention that after writing the first draft of this post and while working on other things, Brett Terpstra published a great post full of tips for better tagging. That is definitely worth checking out if you are considering adding tagging to your setup.