This tells me my system was a good one. Aside from not needing to expand the tag cloud, most tasks I only need to assign 1-2 tags per task, and and tasks inherit one more based on which project I stick them into. My tag filter bar is clean, and small enough to be useful even in lists with lots of tasks. When I posted the list in the Things wiki I got some very positive feedback. But having used the list religiously for a couple months, I have realized something: about 80% of my tags are completely useless.

This is because, up until now, I haven’t brought myself to noticed the obvious:

Tags are only useful if you need to find something.

Of course, it’s hard to tell when you’re first starting to tag whether you’ll actually use those tags down the road to find items easier. That’s actually one of the benefits of tagging: whether or not you use them, they’re easy to add.

The tricky bit is striking a long-term balance: if you tag willy-nilly with the assumption that it’s better to have lots of tags that you might search for someday than to have a few that you’ll definitely search for, you’re very likely to stop tagging sooner rather than later. Tagging may takes very little time but it adds up, and feeling obligated to attach a bunch of tags that you know you’ll never use is a quick route to tagging disillusionment (oh, the horror!).

So what’s to be done? Something really simple: look backwards.

You won’t be able to do this until you’ve been using a tagging tool for a while and you certainly don’t need to do it often, but every once in a while when it comes time to tag something, take a quick break and consider the tags you were planning to use. Have you ever searched for them? Have you even searched for tags similar to them?

When I planned out my grand Things tagging system, I included a subset of tags that described the type of task. I’m a web designer most of the day, so these were tags like “markup”, “styling”, “coding”, “research”, etc. Although I’ve faithfully used these tags with every task I’ve entered, I have never once filtered my list of tasks for any of them.

If I hadn’t taken a moment to look backwards, I might never have noticed this and would have kept wasting my time tagging tasks with tags that aren’t actually relevant to the task’s completion.

Of course, this example isn’t useful in all situations. Particularly in public and collaborative tagging systems, using tags that you’ve never searched for and might never search for can help others. Sometimes it’s a good idea to tag descriptively without worrying about the utility of your tags. But especially if you find yourself using a piece of tagging software that you originally loved less and less often, take a look backwards and ponder whether some of your tagging habits are just cruft that’s weighing you down. When you begin to tag things out of habit and not because the tags are useful, it’s the beginning of the end.

I’ve ordered my copy and will post more about it when it arrives. For more information about the book, check out the Tagging companion website. The book is currently for sale through Amazon.com (I’m not sure whether or not you can find it in brick and mortar stores).

Tags for every situation

1. Tagging for productivity
2. File library vs. file system
3. File system tagging
4. Tagging files with file libraries

I know it’s hardly standard practice to publish things on major holidays, but I wanted to give my U.S. readers something to do while they’re recovering from eating too much turkey, and I can hardly think of a better distraction than an article that I’ve been meaning to write for months, continuing my series of tagging software recommendations. This time the topic is file libraries, and unlike file system tagging solutions, there’s a lot of good options out there.

To recap, a file library is an application that collects, searches, and browses your files outside of the standard Finder and Spotlight interface. File libraries contain some of the best examples of tagging interfaces currently available on the Mac, and thanks to the limitations Spotlight has with regards to tagging often provide streamlined and useful tagging for a variety of file types.

The main contenders

To my mind, there are currently three main contenders if you are looking for a tag-based file library: EagleFiler, Yojimbo, and Together.

EagleFiler ($40) is currently my file library of choice. EagleFiler stores your files in a Finder-friendly format very similar to iTunes (they’re on-disk in a folder of your choosing, but EagleFiler manages them). This (and the pseudo-hierarchical tagging) is perhaps the most attractive feature of EagleFiler. Getting files into EagleFiler is dead easy (usually a single keypress away) and EagleFiler natively supports PDFs, web archives, RTF documents, emails, chats, and more (you can always store unsupported documents in EagleFiler, as well; they just won’t have a preview and you’ll have to edit them in another program). Of particular note is EagleFiler’s support for archiving email; this is a cool feature in and of itself (and not available in the other two), but to make things even better EagleFiler supports MailTags.

EagleFiler’s pseudo-hierarchical tags are one of its main selling points for me. Particularly when it comes to tagging generic files, most programs only support tag clouds which are often little use for people who have a large number of tags. EagleFiler’s tags are not truly hierarchical unfortunately, because the program doesn’t recognize any relationship between parent and child tags, but just being able to sort tags into related groups makes browsing them much easier, and EagleFiler’s developer has mentioned that he may in the future beef up EagleFiler’s hierarchical tagging. EagleFiler’s tagging is complemented by standard-style folders (which are mirrored in the Finder) for those who are not comfortable with a flat, tagged library.

The major downside to EagleFiler is that users cannot create smart views or otherwise save their searches. However, browsing by tag and then using the reasonably powerful search bar are usually enough for me. EagleFiler is not a program to miss if you are looking for simple, powerful, tag-driven document organization.

Yojimbo ($39) is probably the simplest file library you’ll find, but is quite effective despite its simplicity. Yojimbo provides basic tagging and folder-based organization (called “collections” within the program), but does not have any sort of tag browser. Instead, you have to create pseudo-smart view “tag collections” to browse your tagged files. Yojimbo does not store your files in a Finder-friendly format, but in this case it’s a good thing.

Yojimbo’s strength lies not in expansive features or open storage (Yojimbo is, to be honest, pretty bare bones), but rather in the fact that it is phenomenally portable. If you need to access to disparate files and data (such as text documents, images, PDFs, web archives or bookmarks, serial numbers, or passwords) across multiple computers (Mac or PC), then Yojimbo is a solid home run. Not only does it provide synching via .Mac (cool in its own right, when you consider the range of data Yojimbo can handle), but Webjimbo ($29.95) provides a completely web-driven interface into your Yojimbo library from anywhere (including your iPhone).

I wouldn’t recommend Yojimbo for large file libraries or for general tag-based organization, but for keeping yourself connected to your data and files, Yojimbo is the single best solution that I know.

Together ($39; $14.95 upgrade from KIT) is a recently released massive upgrade to KIT (Leopard only, unfortunately). I was never a big fan of KIT. It was completely tag-based, which was cool in theory, but it was as simplistic as Yojimbo without really providing a compelling reason to use it. Together, on the other hand, is a whole new story. Together now permits hierarchical folder organization (mirrored in the Finder), smart groups, a tag-browser that mixes in other types of metadata in addition to tags, tab browsing, and a svelte widescreen-optimized interface that will be instantly familiar to anyone who has used iTunes.

Together provides an excellent merger of form and function. Its tagging is not as good as EagleFiler’s, but its tag-browser-on-steroids provides a kind of power that casual taggers who aren’t totally comfortable with giving up folders will find intuitive and useful. Its interface shares many similarities with Yojimbo in a really good way (particularly the quick import “shelf” that hangs out at the side of the screen) and is all around just a little more inviting than either EagleFiler or Yojimbo. Additionally, Together allows you to move, copy, or simply link to your files, which means that you can, presumably, use it as a searching and browsing front-end to your current file system without modifying your folder hierarchy. Like EagleFiler, Together also easily supports multiple libraries if you want or need to separate your files.

The pseudo-libraries

Although EagleFiler, Yojimbo, or Together is probably what you’re looking for if you’re looking for a file library, there are also a couple other pieces of quality software to consider. They aren’t quite file libraries in the traditional sense, but they aren’t quite file system tagging, either. The culprits: Nifty Box and Leap.

Nifty Box (€24.95) provides a tagging and searching interface for your files, but doesn’t collect or manage them in any way. Instead, adding a file to Nifty Box creates a link to that file. Additionally, tagging files in Nifty Box causes the tags to be added to the file’s Spotlight comments, allowing you to find your files via Spotlight as well as using Nifty Box’s quicker and more efficient tag database. Nifty Box doesn’t have any particularly standout features, but it is a solid possibility if you want something a little more involved than TagBot or Punkea but a little less managed than typical file libraries.

Leap (currently $34, bundled with Yep), currently in public beta, is another pseudo-file library but with slightly more ambitious aims than Nifty Box. Leap ties directly into Spotlight, thus requiring no “importing”. Tags applied in Leap are not attached to files in the Finder (although the developers plan to export tags to Spotlight comments), so if you want to tag or browse via tags you have to it from within the program. On the other hand, Leap has a complex tag browser similar to Togethers, allowing both folders and tags to be browsed as if they were tags. This makes migrating from a complex folder structure to Leap’s tags that much easier, and allows you to find a fair amount of usefulness from Leap without ever having to tag a file.

Leap is advertised as a Finder replacement, and although I don’t think it’s adequate to really replace the Finder, it’s an intriguing way to access your files, and may be a great solution if you don’t want them managed, but still want the lightning fast searching and tag browsing of a file library.

When I was your age, tags was called folders!

Although it pains me to admit it, there are a plethora of options for collecting files and other data that don’t involve tags at all.

DevonThink ($39.95 personal; $79.95 pro; $149.95 pro office) is a favorite for people who like real ultimate power (no, not that kind) when it comes to handling their files. DevonThink’s complexity and price point have always scared me off, but if you’re looking for something with a little more umph than the file libraries above, this may be the one.

Generalized data managers such as VoodooPad, Journler, or Circus Ponies Notebook are also popular places to collect files and data for some people, but I’ll take a dedicated file library any day.

Whatever you end up using, by choosing a tag-based file library to manage your documents, files, emails, and whatever else, you’ll be providing yourself with a searching and browsing experience that Spotlight, Leopard improvements notwithstanding, still can’t match. If you’ve ever wondered if there’s an easier way to store files than your documents folder, you have only to download a good file library to see the difference it can make.

Found the perfect tag-based file library and shocked that I didn’t include it in the list? Give me a shout and let me know the error of my ways! I always love hearing from readers, and any excuse to try a new piece of software is good thing.

This tendency also translates into my advice on tagging. When I came up with the idea of “the what“, it was because I had sat down and tried to think of the most efficient way to tag. The article didn’t come from a system; the system came from the article. But mine is not the only way.

Arnaud Leene notes that “the what” is a very formal way to tag. He’s right; identifying “the what” is a step-by-step process focused on consciously crafting a consistent tagging system. It’s not fun. It’s not flashy. It’s plodding and onerous. When I myself take the time to sit down and identify the attributes that I’m tagging, I feel like some sort of robot. Hello-I-am-tag-o-tron, well-oiled-machine.

I have to admit, though, that not everyone in this world is addicted to logic or methodically moving from point A to point B. In fact, I suspect that most people turn to tagging because they find it easier than using single folders or categories. When you’re tagging, you can just toss any jumble of words on something in the hope that it’ll make finding things easier in the future. Choosing a tag isn’t a life-or-death, here-or-there choice. It’s naming a possibility.

No matter how much you take my advice on finding “the what” (or anything else) to heart, when you’re tagging things in everyday life you should always remember that tagging is about making easy choices. If you find yourself freaking out about what tag to assign to your photo of Aunt Sally, then you may as well not be tagging because you’ll be wasting as much energy and time as if you had thrown the photo in a random folder and then had to search for it later. If you think about “the what” more than you tag, then that system isn’t working for you.

Whether you lean more towards sober planning or random free-loving tag-fests, if you’re able to find the method that makes assigning tags to an item nothing more than several easy choices, you’ll be reaping the benefits of tagging in no time.

Tags for every situation

1. Tagging for productivity
2. File library vs. file system
3. File system tagging
4. Tagging files with file libraries

The fact is that people usually want to tag their files, but unfortunately file system tagging is still one of the most difficult and onerous tagging activities. Although there are a number of different tools now to choose from, if you want to use tags in your file system you will likely need to roll your own solution to some extent.

There are two main categories of file system tagging software: software intended to help you tag your files, and software that you can use to roll your own solution. Keep in mind that the focus of this series of articles is on helping you find software; coming up with a workflow will still be up to you (although I’ll be publishing some workflow advice down the road).

The main two

There are two programs whose entire point is file system tagging: TagBot and Punakea.

TagBot ($20) provides you with a floating palette of tags for drag and drop tagging and a Finder contextual menu. Although you can double click a tag in the palette to open a Smart Folder for that tag, TagBot is primarily useful for tagging (rather than browsing or searching). Tags are stored in Spotlight comments using the popular &tag format (tag name with a “&” prefix). Unfortunately, this means that you can only use single word tags (so get ready to replace those spaces!).

TagBot is not an all-in-one tool, but may be the perfect companion to your other tagging tools; it fits particularly well into Quicksilver tagging systems (more on this later). If you’re using TagBot alone, FileSpot would be an excellent complement, because it uses the same format for tags and picks up searching and browsing where TagBot leaves off (besides having loads of other cool features).

Punakea (free) also uses Spotlight comments, but approaches them very differently: Punakea tags are surrounded by a truly horrific bunch of gobbledy-gook. Although this makes finding tagged files with Spotlight more onerous, it also allows Punakea to offer much more advanced tagging (including multiple word tags). Punakea provides a drag-and-drop sidebar for tagging that conveniently stays out of sight when not in use, and has an excellent cumulative tag cloud for browsing tagged files.

Despite some shortcomings, Punakea is well worth trying out because it is the only software that comes close to being an all-in-one solution for file system tagging. You also can’t beat the price, although the software is still technically in beta and may be buggy.

To be honest, I’m pretty torn between Punakea and TagBot and have not settled on one to use myself. If you prefer a simple tagging solution to supplement your folders and Spotlight use, then TagBot is likely the best solution. If you’d like to try using tagging as your only way of organizing documents (or want a great tag browsing interface), then Punakea is the answer.

Roll yer own

Outside of TagBot and Punakea, Quicksilver (free) is your best solution for file system tagging (it’s possible to use Applescript and LaunchBar for tagging, as well, but Quicksilver has Spotlight comment editing integrated). Some people also like to use Default Folder X ($34.95) to throw tags into the Spotlight comments when they are saving files (further streamlining the process). You may also find Hazel ($21.95) useful for managing files, or even assigning tags automatically, although it will require some creativity on your part to come up with useful rules.

If you’d like an in-depth walkthrough on using Quicksilver and Default Folder X to tag files, try the Apple Blog’s series on using metadata in OS X. Unfortunately, the series doesn’t have any internal navigation, but you can link to all five articles in the series from Tagamac’s tagging resources article.

Of course, you could also eschew all that fancy schmancy software stuff, and just tag files using the Finder’s Get Info window.

Rolling your own file system tagging can be very rewarding; after all, you have complete control over every step of the workflow, so you can craft it to suit yourself. However, it also requires the most energy, thought, and training. If you’d like to roll your own system with the least amount of effort, then you’re likely best off with a combination of Quicksilver, TagBot, and possibly FileSpot. Definitely check out the Apple Blog’s series mentioned above; it’s required reading for Quicksilver-based file system tagging.

But wait, there’s more!

Okay, I kind of lied when I said there were only two applications dedicated to file system tagging. The thing is, there are only two obviously good options. There is a third sort-of-good option, and a slew of stuff that’s unequivocally bad.

The third option is a Java application called Nucle Browser (free) and its companion, the McNucle server. This is actually a very promising project, not least because of its cross-platform nature and ability to remotely access your tagged file system. Of course, I can count the number of decent Java apps that I’ve used on one hand (and wouldn’t be impaired in said counting even if I lost a few fingers), but there you go.

Although my initial experiences with Nucle Browser were very negative, the most recent beta is much more useable. Of course, the double application server/client setup is annoying, as is the occasional unresponsiveness, long launch time, and fact that they store your IP address on their server (which is how you connect the Nucle Browser to the McNucle server). If you can get over these shortcomings, though, it definitely has potential. I wouldn’t recommend Nucle Browser for most users, but if the feature-set sounds intriguing feel free to download it and give it a whirl.

Finally, if you’re really a glutton for punishment, you could try out DropLight, DeskLamp, Branding Iron, or any number of Applescripts. I wouldn’t recommend it, though. Most of this software is scraping the bottom of the barrel, and some of it has somehow managed to bury itself beneath the barrel entirely.

If you’re comfortable defining your own workflow using multiple pieces of software, then you will likely find file system tagging useful and rewarding. If, however, you aren’t interested in putting that much effort into your tagging system or only need to tag a subset of your documents, you may find a file library more to your taste. I’ll be covering file libraries next, so stay tuned, or, if you don’t want my advice, check out file libraries on the software page.

Know of a better way to tag your file system? Let me know! I love to hear from readers, and I’m always looking for new software and workflows to try out.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

Creating a consistent tagging system is like baking a perfect pie crust: it makes you salivate to think about, but some days it just doesn’t work out. Fortunately, consistent tagging (unlike a perfect pie crust) isn’t affected by humidity; all you need is some careful attention to detail. And perhaps the most important detail to keep in mind while you are tagging is “the what”.

Quite simply, the what is just your answer to a two-part question: what item and what attributes? Despite the simplicity of the question, knowing the what is a vital part of creating a consistent tagging system. You can take or leave my SLS guidelines, but if you really want consistency you’re going to have to ask yourself about attributes.

What item?

The first part of the what is usually pretty obvious: are you tagging photos, email, journal entries, characters in your novel, or something else entirely?

Obvious as it may be, deciding what items you are tagging can still require some thought. Although you can generally delineate items based on their file format, there are some exceptions to think about. For instance, JPEGs, PNGs, and GIFs are all images while Word, Pages, and RTF documents are all text documents. When answering “what item?” you’ll need to decide what items to group under a larger heading and which to separate out on their own.

Keep in mind that if you are grouping items you’ll want to use only the most generic groups. Thinking of Pages and Word documents as essays is not useful, even if you only ever write essays in Word and Pages. You may in the future write something in Word that is not an essay, and then your whole way of thinking about tags will get fouled up. When you aren’t using items inside specific programs or individual file formats, use the most general categories of items that you can.

If you’re having some trouble thinking of what items you’re tagging, here’s a list of common ones to get you started:

• Photos (or images) — JPEGs, PNGs, TIFFs, etc.
• Text documents — Word, Pages, RTF, etc.
• Bookmarks (or web pages)
• PDFs
• Email
• Other program-specific items

Once you know what items you are tagging, you can figure out what attributes to tag.

What attributes?

Knowing what attributes you are tagging is the heart of the what, and the key to crafting a consistent tagging system. Basically, you want to identify what you think of when you think of a given type of item. You can do this by looking at items that you have tagged in the past to see trends in what kinds of tags you’re using or by brainstorming out a list of an item’s attributes (or for best results do both).

For example, perhaps you tag text documents based on their status (unfinished, first draft, revised, etc.), their genre (nonfiction, fiction, poetry, etc.), and their type of writing (essay, short story, fragment, etc.). If so, then status, genre, and type of writing are the attributes that you are tagging, and you should try to use them for all text documents (to the extent that it makes sense).

The attributes that you’ll use will differ based on the type of item, so you’ll have to come up with a unique list for each item type. Make sure not to use any attributes that are already available in the item’s metadata (after all, there’s more to life than tags).

Once you have your list of attributes for each type of item, you’ll need to decide which attributes on the list are worth tagging. After all, if you think of a text document’s subject but are never going to search for text documents based on subject then there’s no reason to use a subject tag.

At last, though, you should have an idea of what attributes you want to tag for any given type of item, and then all that’s left is to consistently tag based on those attributes. This will help you in two ways: first, you don’t have to waste time and energy when you’re tagging new items trying to figure out what tags to use because you’ll know which attributes you should tag. Second, you’ll know what kind of tags to search or browse for to find different kinds of items. And perhaps best of all, you’ll have a set of general guidelines based on your unique way of thinking about tagged items that will stay consistent over time.

There will of course be cases where you’ll not use an attribute for an item or will use another attribute, but in general knowing the what will allow you to keep your tags much more consistent than if you were just throwing tags on items based on your feelings and thoughts of the moment.

Finding the what

There’s no one correct way to find the what. Some people may want to sit down before they start tagging at all and deliberately map out a list of attributes for each type of item they will tag. If you do this, you’ll likely have a very consistent and well thought out tagging system. However, you could also just keep the what in mind while you’re tagging and observe what attributes you tend to use. It’ll be sloppier, but you’ll still end up with a more consistent tagging system than you would otherwise.

One last thing to remember is that the what will change over time. New software will come out and you’ll think of new ways to organize items or begin to think about tagged items differently. Even if you take the deliberate road and create a list of attributes to tag, you’ll need to be flexible. Putting some effort into figuring out the what early on will certainly be worthwhile, but there is ultimately no fighting the vicissitudes of time and the human brain.

Tags for every situation

1. Tagging for productivity
2. File library vs. file system
3. File system tagging
4. Tagging files with file libraries

Although tagging for productivity can be fun, tagging any old file on their computer is one of the main things people want to be able to do (right up there with tagging photos). If you’re into tagging your files, then you’ve probably run across two different ways to do it: file system tagging and file libraries. I’ll get to specific software in the next article; for now, here’s the differences between the two.

Wether you use file system tagging or a file library depends mostly on personal preference. Both have their pros and cons, and both have a selection of different software available (although file system tagging still doesn’t have any standout fantastic options).

File system tagging

If you use file system tagging, you’ll attach tags to your files so that you can find those files in the Finder or using Spotlight. At the time of this writing, there is no good way to store keywords or tags via Spotlight, so most file system tagging options make use of Spotlight comments.

File system tagging complements folder-based organization, and is quite forgiving (and usually cheaper) because it makes use of features provided by the OS. File system tagging software complements the operating system rather than replacing its functionality. Using file system tagging, you can tag virtually anything in your computer using a single tagging system.

The downside is that there is no great software for file system tagging. Some of the software is quite good, but nothing has been released yet that makes file system tagging as enjoyable and easy as it should be. Some developers are hoping that OS 10.5 will introduce features to Spotlight and the Finder to make file system tagging easier to implement; currently being stuck with Spotlight comments is the main hurdle for file system tagging software, and the reason that it is so universally limited. Until that time, though, file system tagging will likely remain somewhat clumsy to implement.

File libraries

A file library collects and searches your files outside of the Finder and Spotlight (although most file libraries are integrated with Spotlight to some extent). In general, if you’re using a file library you’ll be storing your files in a program-specific database.

The best part about using a file library is that its searching and browsing will be much more efficient than using Spotlight or file system tagging software. Additionally, the tagging capabilities (and other organizational tools) are universally better than anything file system tagging has provided because the developers have complete control over how they attach information to files.

The downside is that file libraries are often harder to integrate with other software. Tagging a file in a Spotlight comment means that any program that accesses Spotlight comments can use the tag. Tagging a file in a file library usually means that the tag can only be accessed if you’re running the file library (or, to a limited extent, through Spotlight searches). If you start using a file library, you’re making a commitment to keep using that specific file library.

Which to use?

Currently, file libraries are far easier to use because they provide an easy workflow out of the box, such as it were. Once you’ve learned the tools and interface, a file library can make tagging files extremely simple. File system tagging is not quite so friendly because to get a really good workflow you have to put a fair amount of creative work into the process. If you are able to develop a good file system tagging workflow, of course, it can easily end up being more universally applicable to files than a file library. You just have to be willing to put in the time.

I’ll be covering specific options for file system tagging and file libraries in a forthcoming article, so stay tuned!

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

I’ve said it before and I’ll say it again: tags are an extremely flexible way to organize the mad rush of information that is your computer. As you no doubt have picked up (from the existence of this blog, if nothing else), I have a bit of a love affair with tags.

However, while tag-love is a special and beautiful thing, if you are going to create a really great tagging system one of the most important things you have to know is when not to tag.

Remembering that there’s more to life than tags is sometimes difficult, particularly if you’ve just discovered tags and had that little “ah-ha!” moment when you realized that folders are not the only way (if you haven’t had this moment, take it from me: it’s a good one). Many converts to tagging, in their zeal to jump into a new system of organization, forget a simple fact: tags are the least effective metadata you have available to use.

This is because most metadata comes in key / value pairs. The key is what the information is (for example, the date a document was created), and the value is the information specific to the item (for example, I have a text document on my computer that was created on Dec. 17, 2005). Key / value metadata is really useful, because you can search a specific key based on a specific value, so you know exactly what kind of items you should find. Custom searches can be targeted very effectively using key / value metadata.

Tags, unlike most metadata, are just a value. Unless you get tricky with your tagging, a tag contains no information about what it represents. If I tag a photo “paris” it could be the city or the celebrity, and until I’ve looked at each of the photos that my search turns up I won’t know.

Because searching through key / value metadata is far more effective than searching through tags, you need to make sure you know what kinds of metadata are already attached to the items you are tagging. Unless you’ve made a conscious effort not to duplicate information from key / value metadata in your tags, you may well discover that tagging and finding items is more of a head-ache than it’s worth.

There are several ways you can find out what metadata is attached to an item before you begin tagging. The Finder’s Get Info window is an excellent place to discover the basic, automatic information that gets attached to every file on your computer. You can also choose File→New Smart Folder in the Finder to see some of the information that you can easily search. Third party Spotlight extenders like FileSpot can help even more in this regard. In iPhoto, you can find the large amount of information automatically attached to photographs by selecting a photograph and choosing Photos→Get Info or hitting command-I. Most other programs that include tags have some sort of key / value metadata attached to items, as well. You just have to find it. (The shortcut command-I is fairly prevalent for getting such info; if you’re at a loss, just try it to see what happens.)

Once you’ve figured out what metadata is already attached to a type of item, then when you’re tagging those items you should make a conscious effort not to duplicate that metadata.

Tags are amazing and flexible, but unless you know when not to tag they will make your life needlessly complicated.

Tags for every situation

1. Tagging for productivity
2. File library vs. file system
3. File system tagging
4. Tagging files with file libraries

I suppose I’ve put off talking about the actual tools you’ll use for tagging long enough. It’s time to do a run-down of the available tagging software with some advice from your’s truly on whether it’s worth using or not.

This series will focus on the different areas where you might be tagging: productivity (read: miscellaneous), file libraries and the file system, photos, bookmarks, and general writing. These articles will not contain specific workflow examples, however; I’m just pointing out the tools you can use. I’ll get to how best to actually use them later.

I’m starting with my miscellaneous category because it contains what is essentially the One True Tagging Tool on the Mac: MailTags.

MailTags is not a perfect example of tagging or browsing (some of its failings are that it has auto-completion on single emails only, a clumsy contextual menu for multiple emails, and only allows searches or saved searches to locate items). However, it is still quite possibly the most useful tagging implementation on the Mac. Other programs make a point of stating that they are compatible with MailTags. That’s how cool it is.

The reason MailTags is so useful is because it does more than just tagging. The tagging, if you use it carefully and thoughtfully, will make locating and filing emails a lot easier and simpler than the old folder system (hint: define some rules to apply tags, and do it early). MailTags also offers iCal integration, project management, and more, which is what makes it really stand out as a must-have app. This is perhaps a useful object lesson: you can do a lot of cool stuff with tags, but the best tagging software will implement tagging into a larger picture.

Next up is iGTD, the “getting things done” app from Bartek Bargiel. Although I’ve written an in-depth review of iGTD, the short version is that iGTD is a very powerful application that is overly complicated to use. Tagging in particular seems like a feature that is of limited usefulness, although the integration with MailTags is definitely a big plus.

If you do much coding, you might want to try out Code Collector Pro, an app that stores snippets of code and sports a number of fun features beyond tags, such as support for TextMate syntax coloring bundles. Tags and smart views are the main organization within the program, and work nicely. Although text expanding programs or TextMate snippets might serve you just as well, Code Collector Pro is definitely worth a look-see if you need a quick and easy way to track reusable snippets of code.

Finances in need of some tags to make sorting them out easier? Check out Cha-Ching. Although the program is nowhere near as powerful as many financial managers, it is a lot simpler and it has a nice tagging implementation with useful and simple smart folders. I’ve been using it for a month or two and been overall pretty happy with it. Then again, my needs are simple and I’m biased towards tags.

Should you enjoy using 37signal’s Backpack service you should definitely check out PackRat, a desktop client to the web-based Backpack. I am not a big Backpack fan, but it can definitely be a useful service, and PackRat brings it offline; always a nice addition to a sweet web 2.0 application.

Of course, this is hardly an exhaustive list of tagging programs that can help your productivity out, but most of the others can be more easily categorized. Next up I’ll be covering those favorites of tagging junkies: file libraries and file system tagging.

Defining tagging

1. The parts of tagging
2. Tag browsers
3. The realms of tagging

Tagging as a popular phenomenon was developed online, where many tagging systems feature tags created by the members of a site. Thanks to this phenomenon, a lot of the intellectual thought about tagging centers around “folksonomies” and other ideas of collaborative tagging.

However, there are actually three distinct realms of tagging, and each requires you think about tagging in a slightly different way: private, public, and collaborative.

All three realms are hopefully somewhat self-explanatory, but there are some interesting things to note about each.

Private

A private tagging system is one where a single individual tags items, searches for items, and browses for items. This is the single easiest type of tagging, because it requires the least thought. You can tag things the way you think about them without worrying how other people may think.

Private tagging systems are most often found in desktop software, but occasionally do make their way online. A lot of the early advice that I’ve published on Tagamac assumes that you are crafting a personal tagging system because of my early focus with Tagamac on desktop tagging.

Public

A public tagging system is created and maintained by a single individual, but other people can search and browse the tags. An excellent example is the tags on every Tagamac article: I’m in complete control of them, but they are intended for the benefit of other people.

Public tagging is trickier than private tagging because besides being consistent, you also have to consider how the other people will use tags when browsing and searching, and tag accordingly. For example, my advice to keep tags singular may not be a good idea in public tagging, where people tend to think of tags as categories rather than information attached to a specific item.

It’s worth noting that you may well make different choices when tagging if the other users are searching or browsing for tags. In a browsing system, you don’t have to worry quite as much at what might be the terms that come first to mind for your visitors, because they’ll have all the terms in front of them. If it is a searching system, though, you’ll have to keep the ways your visitors might be thinking firmly in the forefront of your mind.

Collaborative

In a collaborative tagging system every user tags items. This kind of system is fairly prevalent online. “Folksonomy” is often used to refer to collaborative tagging.

Collaborative tagging has a lot of strengths, but consistency is usually not one of them. Because everyone tags differently, tags can quickly become a giant mess. On the other hand, if the user base is large enough items tend to be tagged more thoroughly than in either a private or public system. Generally, if you are contributing to a collaborative tagging system (such as del.icio.us or Flickr) you should try to keep your personal tagging system consistent (to maintain your own sanity) and also try to consistently use the tagging conventions that have evolved in the tagging system you’re using.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

Sadly, not all tagging software is coded equal. Sometimes tags are thrown in as just one more bell or whistle, intended to plump up a feature-set without being particularly useful. Other times developers don’t understand tags themselves and end up implementing them in a way that is not as friendly as it should be. Sometimes supporting spaces in tags causes other problems (such is the case when trying to roll your own tagging system using Spotlight comments).

In any case, you may well run across a piece of tagging software that does not allow you to use spaces in your tags, which can be a major pain in the nether regions. What you do about it is really up to you (although of course I have some suggestions), but when you decide remember the tagging mantra: consistency, consistency, consistency. Pick something and stick with it.

Developers disallow spaces in tags for any number of reasons. Some, such as the difficulties with Spotlight comments, are totally legit and you just have to work around them. Others, such as the idea that tags should only ever be a single word, merely show that they don’t really understand tagging (sometimes it is impossible to use a single word; for instance, when I’m using Cha-Ching to file my financial expenses, I need to tag some of them “one crayon” so I know it’s a One Crayon business expense; thankfully, Cha-Ching is friendly about spaces). In these cases, file those feature requests!

Whatever the reasons, we’re living in the present and not some perfect world of the future, so your best option is to use some character to substitute for a space.

I highly recommend the underscore. Underscores have been a standard space replacement online for quite some time; it looks kind of like a space, it’s about the same size as a space, and it doesn’t really have any other practical usage now that typewriters are out of fashion.

Other good options are the hyphen and the plus sign, but they are less desirable for two reasons: 1) they are more intrusive when it comes to reading the tag, and 2) they are sometimes used for more powerful searching. Of course, if the software developer disallowed spaces, then they may well not support AND/OR and NOT searching, but you never know what the future may hold.

Another option, of course, is to go wiki-style and use camel case (for example: “ShortStory”). I personally advise against this because it opens up an even nastier can of worms than normal in the lowercase/uppercase debate (do you capitalize the first word or not? What about for proper nouns?), but it is as always up to you.

If you are lucky, of course, the software will be friendly enough to substitute an underscore when you hit the spacebar (instead of completing the tag). But if not, go with the underscore anyway. It’s a winner.

I will try to get some software recommendations and reviews written in the near future, but it may be some time before I’m able to jump headfirst into real workflows. In the meantime, I’d like to offer some good resources elsewhere on the web that you can use to get your tagging system off the ground. Sadly, I haven’t been able to locate many good resources (which is a big reason I started Tagamac, actually), but at least there’s a few.

Probably your best bet when thinking about tagging is The Apple Blog’s wonderful, step-by-step overview of file system tagging using Quicksilver and Default Folder X. Here are the links to the complete five part series:

• Part One: Using Metadata Effectively
• Part Two: The Tools
• Part Three: Screencast
• Part Four: Answering Screencast Questions
• Part Five: Wrap Up

If you are interested in collaborative or public tagging (through services such as del.icio.us), then you may find Wired’s Tips from Top Taggers or TechSoup’s Thirteen Tips for Effective Tagging interesting.

I’ve found some other articles on tagging, but they tend to either focus on very limited tagging systems (such as those on a single website), or not provide much of use. If you know of any other great articles or websites that offer good tips on tagging, please let me know! I don’t want to leave anyone out in the cold while I’m working on my great crusade to create a full and complete tagging resource, but I certainly don’t have encyclopedic knowledge of everything that’s been written about tags.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

Since I published my advice on tagging best practices, the most common question I’ve received has been something along the lines of “why the heck would you use singular tags?” Everyone agrees that consistency is the name of the game, and it’s hard to argue with succinctness. Some people disagree with using lowercase tags, but quite honestly it’s mainly personal preference (unless the program uses case-sensitive searching).

Whether or not to use singular tags, though, is a much more open question, and I’d like to lay out the reasons that I included a recommendation to stick to singular.

First I should mention that I don’t think every tag should be singular; whether or not you use singular tags is highly situational. For instance, if you have a photograph with a group of people in it, then tagging it “person” is utterly ridiculous. When I advise using singular tags, my hope is that people will try to stick to singular tags only when appropriate. If singular tags are the baseline, then searching for “people” as opposed to “person” means you get two different sets of items rather than one set of items that includes both. (Of course it can work the other way if you use plural tags as your baseline, too. Whatever makes the most sense to you is what matters.)

Second, a major assumption that I held going into the best practices article was that you are tagging items in a desktop program for personal usage. In this case, there is no question over what you will search for because you have complete control over all three parts of tagging. However, if you are tagging items so that other people will find them (the case in most online tagging), you will need to think about tags differently. Sticking to plural tags may actually benefit you more for online tagging, because people tend to think of tags online as categories. Neglecting to mention that my SLS guidelines are most appropriate for personal use was an oversight of mine; there are large differences between personal, public, and collaborative tagging.

Ideally, of course, your tagging software would permit creating synonyms for tags. Unfortunately, we don’t live in an ideal world, and this is pretty rare (might even be non-existent; off the top of my head I can’t think of any software that supports tag synonyms).

At base, whether you tag by default with singular or plural really relies on how you think about tags: are you tagging what an item is or what an item is one of? In the first case, you should use singular as much as you can. In the second, you should stick to plural. For example, I could tag this article “clarification” because I am clarifying an earlier argument. Or I could decide that my “clarification” tag is more like a category; it contains multiple items, each of which is a clarification. In that case, I would tag this post “clarifications”.

I personally prefer to use singular tags as my default because I think of tags as terms that describe a specific item. For me, a tag says, “This item is a [blank]“. I am not sorting items into categories; rather I am attaching descriptive terms to items. The wonderful thing about tags, though, is that if thinking about tags like this makes no sense to you, you don’t have to follow my advise.

I knew when I included both lowercase and singular into my little “SLS” scheme that they were mostly reliant on individual preference. The reason that I included them, however, is because both the capitalization and plurality of your tags are things you must consider when you are building a tagging system. I don’t care whether you tag things the way I do; what I care about is that you think about the issue before you start tagging inconsistently and causing a lot of pain for yourself.

I hope this has helped to clarify my standpoint on the plurality of tags! If you have any thoughts on the matter, I would love to hear from you!

Defining tagging

1. The parts of tagging
2. Tag browsers
3. The realms of tagging

One of the reasons that tagging can be difficult to get into is because few tagging systems are alike. Although there are similarities, tagging is not only still evolving as a way of organizing but there are also several different ways to think about tags.

The most striking difference between different tagging programs is generally the tag browser. The act of tagging is fairly standardized (auto-complete, drag and drop, etc.), but browsing is much more heterogeneous. Most browsers fall into one of three types: tag clouds, tag trees, or tag recipes.

Tag cloud

The tag cloud is the most common tag browser online and is also well represented offline. A tag cloud is a list of all available tags, often with some indication through color or size about which tags are used more (the tags are weighted).

A tag cloud is flat; in other words, the tags have no direct relationship to one another. If I’m using a tag cloud to sort RTF documents, the tagging software may know that “writing” and “short story” occur on a lot of documents together, but it doesn’t know that a short story is a type of writing.

Some tag clouds allow you to browse for single tags, while others are cumulative. A cumulative tag cloud lets you select multiple tags and find only items that have all of them. Tagamac’s tag cloud is not cumulative, but it is a good example of a weighted cloud (using size rather than color).

Tag tree

Tag trees are less common online (I’m not sure if I’ve ever come across one, actually), and more common in software that manages things like photos. Tag trees are hierarchical. Tags can contain other tags, and they move from general to specific. For instance, I might have a “country” tag and inside of it I have tags like “france”, “britain”, and “swaziland”. Then inside of those tags I might have cities: “paris”, “london”, and “mbabane”. The tags have a parent-child relationship: “britain” is the parent of “london” and “mbabane” is the child of “swaziland”.

Tag trees are not good for cumulative browsing. Instead they allow you to drill down to a specific tag, which limits your results to items that have that tag. The advantage of using a tag tree rather than a traditional hierarchical system (such as folders) is that items can easily have multiple tags.

Some tag trees allow you to see the contents of children tags when browsing a parent tag. Others subscribe to traditional folder styles and only show you the items that have that specific tag. Both ways have their pros and cons.

Tag recipe

Tag recipes are usually found in desktop software. Browsing a tag recipe is like finding a recipe by selecting the ingredients one by one. First, you select a single tag. You are then shown a list of all other tags that occur on items with the first tag. You continue to select tags until you have a recipe of tags and a very small number of applicable items. Tag recipes can easily be paired with either tag trees or tag clouds.

Tag recipes are flat because they only show which tags occur together with no indication of parent-child relationships, and they are always cumulative. The nice thing about a tag recipe as compared to a cumulative tag cloud is that the recipe only lets you pick tags that occur together.

As far as I know, I’m the only person who uses the term “tag recipe.” There may be a more technical term for them, but I wanted something that suggested its functionality. Of course, the metaphor is a bit backwards unless you do a lot of searching for recipes using ingredients, but such is life. I’d love to hear if you know of another name for this kind of tag browser. The only other one I’ve heard bandied about is “tag browser”, which applies to all three to my mind.

Why do we care?

As I’ve said before, there’s no single right way to tag. How to tag relies heavily on which tag browser you are using and what makes sense to you. The tag browser is usually what makes or breaks a piece of tagging software, so knowing what your different options are can help you find the perfect software for you. If you know that using tag clouds makes you irritable (or joyful, or melancholy, or whatever else), then you can save yourself a lot of time when you are browsing through software.

Defining tagging

1. The parts of tagging
2. Tag browsers
3. The realms of tagging

I like to think that tagging is straightforward. It may seem like a strange way to organize and find information at first, but once you get used to it the whole process is not that complicated.

However, even when a subject is not particularly complicated, it can still be difficult to talk about. I have found in my journey through life (and academia, which are not one and the same no matter what they tell you) that one of the most important parts of any discussion of a topic is solid definitions. As a result, I am going to try to break down using tags into simple definitions over the course of several articles. This article is the first, and defines the three actions that you will perform when working with tags:

Tagging: the act of attaching a tag to something. This is probably what you think of first when you think of tags. Tagging also refers to maintenance of your pool of tags; removing tags, renaming tags, organizing tags, adding new tags, etc. Tagging is the creative portion of using tags, because you have to think up which tags to use (also when you are thinking of using the SLS system or not).

Searching: the act of using tags to find specific targeted items. You could also call this “filtering” if you wanted. Searching is what you do when you know what you are trying to find, and you use tags to locate it. An example would be if I wanted to find that picture of my friend Suzy that I took in New York, and searched for items with the tags “suzy” and “new york”. Searching also covers using saved searches to sort and locate items.

Browsing: the act of using tags to find related items. Unlike searching, browsing doesn’t target any specific item or subset of items. Instead, when you browse tags you are usually looking for related items. For example, I might browse my “suzy” tag to see all pictures of Suzy. Closer to home, the tags attached to each article on Tagamac are best suited for browsing because while they do not supplement the search system (and are thus not very useful for locating specific articles), they do make it easy to find articles that are related.

Tagging guidelines

1. Tagging best practices
2. A singular question
3. Replacing spaces
4. More to life than tags
5. The what

In all honesty, best practices for tagging vary greatly depending on the type of tagging system and tag browser you are using. Additionally, because tags are so flexible, how you use them also relies a lot on what makes sense to you. There are still some things you should think about when you tag, though, and I think they’re important enough that I’m posting them now before I dive more in-depth into tags.

First off is tagging’s golden rule: be consistent. You can disregard every other piece of advice I give you, but consistency is the single thing you must strive for when tagging. Everything else is window dressing. That said, here are three things that I think almost every tag should be, regardless of what program or system you’re using: succinct, lowercase, and singular.

Succinct

Of the three, this is the one that is absolutely necessary. Tags must be short, simple, and memorable. Always pick a single word over a phrase. Pick a word that is the most descriptive you can think of, but is also one you will remember later. Never use a complicated word when a simple one will work.

A succinct tag is easier to remember when you are tagging later items or searching, quicker to comprehend when you’re scanning through tags, and improves your sex appeal.

Alright, so good tagging and sex appeal aren’t actually related; you get the point. Be succinct.

Lowercase

Keeping all of your tags lowercase is a really, really good idea, but you won’t be struck by lightning or anything if you capitalize them. The main reason to stick with lowercase is consistency. Not only are tags generally lowercase by convention (which means some programs may have difficulties with upper case letters in tags), but lowercase is a better default.

For one thing, if you keep all your tags lowercase, then it is impossible to have problems with a program mistakenly matching the case of a tag. For another, it is easier to maintain consistency if you always use lowercase letters. Capitalizing only proper nouns may work, but down the road you may change which words you capitalize or use capitalization inconsistently with some words. And hey, lowercase letters are just quicker to type.

You don’t have to keep everything lowercase, but I strongly recommend it (grammar-Nazi that I am, when I first started using tags I capitalized proper nouns; then I sat down and thought about it and realized I was being a bit silly).

Singular

Of my three best practice guidelines, this is the one that you’ll ignore the most. The reason that I include it at all is that you should only use plural tags when absolutely necessary. If you stick to singular words by default, then it reduces the questions you may have when searching your tags. “Did I tag that photo ‘people’ or ‘person’?” is a question that wastes your time and adds unnecessary difficulty to tagging.

By consciously making an effort to keep everything single, you will improve your ability to find exactly what you are looking for, which is what tags are all about. There are certainly times when you should use a plural tag; just make it count.

Consistency

At root having “SLS” tags is really all about consistency. By keeping your tags succinct, lowercase, and singular, you’ll be making it easier to search them and tag similar items consistently.

There is, however, a lot of variation in how to tag an item. Whether you use specific or general tags, more or fewer tags, and redundant or distinct tags has more to do with the software you are using than anything else. But that’s a topic for another time; for now, I hope you will find the idea of SLS tags useful!