I don’t give up easily, though, and ever since I relaunched Beckism.com (which as of the relaunch is completely authored in MarsEdit) I’ve been noticing that I’m updating Beckism.com more often than Tagamac because it’s easier. It was time to do something about this, particularly because Tagamac is far more popular, so I hacked away at MarsEdit’s plist and will from here on will be authoring Tagamac using MarsEdit instead of WordPress’s web interface. For those in a similar predicament, I’ve written up a guide on migrating images into MarsEdit, published over at Beckism.com.

Check out the new design or read the redesign announcement for yourself! If you’ve visited before, I think you’ll be pleasantly surprised.

But don’t wait until version 4! If you want access to some of Default Folder X’s sweet capabilities now, you’re in luck. St. Clair Software has an upgrade policy that will allow you a free upgrade to version 4 if you buy version 3.0.6 now. Version 3 is fully Leopard compatible (as long as you aren’t running any 64-bit apps); it just lacks the translucency. For more information, and to download Default Folder X 3.0.6, see the Default Folder X website.

So take a break from tagging those pesky files, head over to Bill’s website, suggest a name for his lost dog, and win yourself a great novel. Or lose and buy it anyway. Whatever works for you. And with that minor endorsement out of the way, I’ll see if I can’t write something pithy about tagging next.

There are some similar aspects to all GTD task managers, but I think one of the primary deciding factors whether or not a particular piece of software will work for you is how much structure you need or desire. With that in mind, here’s the GTD software for Mac OS X, ordered from most structured to least: Midnight Inbox, OmniFocus, iGTD, TaskPaper, iGTD 2 (early development), and Things (approaching public preview). If you’re like me and agonize over task managers, then this is a pretty daunting list (and if you count some of the less polished options, it’s nowhere near complete). However, with an eye to structure, I don’t think it is all that difficult to narrow the list down to a couple of applications that you should try.

Just what is “structure,” anyway?

Structure in a GTD app applies both to the metadata attached to tasks (do tasks have contexts attached? Tags? Priorities?) and to the workflow that the application’s interface encourages (are you encouraged to focus on projects, or focus on tasks that you need to do today?). Some applications give the user very specific information and a very specific workflow (the more structured apps), while others allow much more freedom (the less structured).

For some people, the highly structured apps will be the most appealing because the workflow and information attached to tasks makes perfect sense to them. For others (myself included), the less structured apps will be more inviting because they allow the user to craft a more personalized system (and are often less complex for users who don’t want to use the advanced features).

Figuring out whether you prefer more or less structured approaches to GTD is something everyone will have to do on their own. Odds are if a screencast or feature list for a given application makes you think, “Wow!” and start imagining what you could do with it, that’s the type of application for you.

But enough with generalities! Let’s take a look at the actual applications side-by-side.

Structure to live by: projects and contexts

Midnight Inbox ($35) is by far the most structured of the available apps, and it is also one of the few polished GTD apps available (and has been available for some time, unlike the still-in-development OmniFocus). Personally I think that using Midnight Inbox is like having David Allen standing behind you, twisting your arm, and shouting in your ear, “Do it my way!” That said, if a five-step, context-oriented task workflow makes sense to you and you’re willing to let the software know best and collect what it thinks you need to organize, then Midnight Inbox is worth a look. It’s certainly a polished-looking piece of software, and is one of the few GTD applications available as a stable, tested release.

Midnight Inbox’s biggest strength (which also happens to be its biggest failing) is that it can collect practically anything on your computer automatically (email messages, iCal to-dos, text documents in a specific folder, etc.) and encourage you to review them for actionable tasks. This can be really handy, but for myself I’d just end up frittering away all my time collecting, organizing, and reviewing tasks rather than completing them.

OmniFocus ($39.95 prerelease; $79.95 standard) is nowhere near as controlling as Midnight Inbox, but it is still highly structured around projects and contexts. Tasks have quite a lot of specific metadata attached to them, but are displayed in an easy-to-understand outline similar to OmniOutliner.

OmniFocus is another app where, for me, there’s a little too much complexity (bringing about a “I’m not getting any work done because I’m constantly playing with OmniFocus” type of workflow). In its defense, OmniFocus does provide an inviting interface to tempt you in, and with complexity comes great power. If working out of contexts and projects makes sense to you, then OmniFocus is probably your best option, if only because of Omni’s attention to detail, great interface design (overlooking, for the moment, their obsession with inspector windows), and dedicated support team.

An unfortunate result of OmniFocus being the only one of these apps that is produced by a larger company (compared to the individuals and small teams working on the other apps) is that its price will be less competitive when it finally goes release candidate. At the time of this writing, there’s a lot of pressure to just buy OmniFocus without really being able to experiment with the other options because the prerelease price is half what it will cost after January 8, 2008.

Then there’s iGTD (free). I have a love/hate relationship with iGTD. It has a lot of power, but terrible interface design. Balancing that out, it’s free, which is a pretty tempting price point. iGTD has a far worse learning curve than OmniFocus and is plagued by many of the same problems (as far as restricting you to contexts and projects). It additionally has a bad case of feature bloat which OmniFocus, while pretty overwhelming at first glance, has minimized.

If none of the other options look like they’ll provide the power you need to manage your tasks, then iGTD is very likely the perfect program for you. It integrates with just about everything (notably MailTags) and provides more metadata than you ever knew you needed. However, particularly given the brief glimpses we’ve had of iGTD 2, iGTD looks like it will be badly outclassed in the very near future.

Straddling the fence between the more structured and less structured apps is TaskPaper ($18.95 intro price). TaskPaper is by far the least complex GTD task manager available, and if all you need to do is jot down lists of tasks sorted by basic projects and tags, then TaskPaper is probably the perfect solution for you. TaskPaper doesn’t compete with the other GTD apps as much as it provides an interesting counterpoint in task management minimalism. It is extremely limited, but a perfect step up from plain text lists for some people. Unfortunately, its tagging is only really effective when used similar to OmniFocus/iGTD contexts

I’ve actually been using TaskPaper as my primary task manager for the last few weeks just to see if I could, and it’s been an interesting experience. On the one hand, using TaskPaper made me realize that I don’t need a really complicated solution. On the other, it turned out that some features from the other GTD apps are things that I want. I highly recommend using TaskPaper for anyone who has tried a number of GTD task managers without being able to pick one. It’s an experience that really helps clarify your needs.

Laid-back structure: focus and tags

As much as I wish it were otherwise, the two less structured GTD apps have not yet been released to the public.

Although there has yet been nothing except preview screenshots and short screencasts, iGTD 2 (forthcoming; free) is looking like a solid step in the right direction for iGTD. iGTD 2 looks like it will abandon the standard project/context framework supplied by the many other apps in favor of tags and “focus.” Focusing on tasks, a central component of both iGTD 2 and Things, is basically looking at tasks based on general shared characteristics (such as tasks that need to be done next versus tasks that need to be done today).

Not only is iGTD 2 much less structured than other available apps, but it looks like it will be pulling on some of the immense power of iGTD, but filtering it through an interface that is far, far superior. The tabs and saved workspaces in particular are a pretty ingenious approach to viewing complex assortments of tasks. I also think that its attempt to use natural language for its interface elements is bang on target, and may well help iGTD 2 to dip into the more casual task manager crowd that iGTD is currently alienating through its complexity.

And finally we get to Things (forthcoming; pricing as yet unannounced), the least structured of all the task managers. Like TaskPaper, one of Things’s goals is to simplify task management. However, unlike TaskPaper, Things still provides a lot of potential power through its versatile and intuitive tagging system. Things doesn’t yet provide feature parity with some of the more structured applications; what it provides instead is an elegant and easy-to-use system for sorting and accomplishing tasks that scales to the complexity the user wishes to have.

Things still has a definite structure, of course; it provides an interface that expects your workflow to include steps like collecting tasks, organizing tasks, and then completing tasks like most of the other GTD managers. Tagging (and Things’s intuitive tag filtering) is what allows more freedom in Things structure than within, for instance, OmniFocus’s strictly defined metadata.

Which solution?

If you know whether structure appeals to you or not, you should hopefully now have a better idea of which GTD apps are the most worth the time it takes to evaluate. Thinking about task managers in terms of how they structure tasks and workflow is a much different way to think about software than most people are used to (feature comparisons are much more standard), but I think it’s one of the most important things to think about for an application that is so intimately related to the actions that you take in your life.

Of course, features are important, too. The applications with the most features (and thus the most complexity) are probably iGTD and OmniFocus. Things and iGTD 2 are difficult to evaluate based on features because neither is feature complete yet. Midnight Inbox is fairly feature-rich but in an all-in-one-solution way, and TaskPaper almost doesn’t have features at all (in a good way).

The truth of the matter is that it still isn’t possible to compare OmniFocus vs. Things vs. iGTD or iGTD 2. Until we have at least a 1.0 release candidate for all of the main contenders, it will be very hard to compare features and performance, which is why I avoided trying to compare specific features of any of the applications.

Just looking at the software that’s publicly available, iGTD and OmniFocus are the best choices if you need a feature-rich application, and TaskPaper is the best stopgap for people with simpler needs. Depending on how many features Cultured Code is able to cram into its public preview version of Things, Things may also be able to serve some people before it is released.

Although I’m really looking forward to the less structured software (I do love my tags), if you prefer a structured solution to task management you may be able to find the perfect application without much more ado. Whatever your preferences, good luck! Finding the task manager that works for you can be a difficult and time-consuming process, so I hope that this general comparison has helped you slim down the options somewhat.

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.

Definitely a useful article to read if you use Spotlight much (for finding tagged files, for instance), although it doesn’t have anything to do with tagging specifically. (Thanks to Daring Fireball for the link.)

Although Hawk Wings is usually focused on Mail.app, it also often provides information about productivity software more generally, so even if you’re not a Mail.app fan, check it out!

I haven’t heard word yet what the changes to the metadata are like (the big question: will tagging system files be easier?), but hopefully the metadata will be more tag-friendly and we can get away from the ever-so-imperfect Spotlight comment. I will of course be posting more information as it comes available, and once my copy arrives I’ll try to suss out the metadata changes (if any) as soon as I can.

I’ve finally finished writing up my own list of 35 essential Mac apps, posted over on Beckism.com. There’s some overlap with Freelance Switch, and some of the really good stuff from Freelance Switch didn’t make it on because I personally don’t find it particularly essential, so you’ll probably want to check out both lists. Of course, it doesn’t have much to do with tagging (I haven’t needed tagging software for my freelance work, so there isn’t much tagging software on the list), but I figured you’d be interested nonetheless. Enjoy!

Well, sort of. Unfortunately, WordPress 2.3 is very bare bones when it comes to tags. No auto-completion. No cloud underneath your editing window. You have to either remember all of your tags, or just go for broke with the random method.

Thankfully there are, as always, plugins to make WordPress behave the way you want. Two that I highly recommend are Tag Managing Thing from the creator of the Ultimate Tag Warrior and Recommended Tags.

Tag Managing Thing does pretty much what it says, and not only allows you to manage tags but also categories. Very useful for changing names and slugs, merging, splitting, or otherwise manipulating your metadata.

Recommended Tags brings auto-completion, recommended tags based on some Javascript voodoo, and a list of all tags in the site to easily add tags to posts. You can choose the functionality that you want to show up on your posts page, making it even more useful and friendly.

Also, if you’re updating to 2.3 don’t miss the overlooked tag template tags is_tag() &emdash; a conditional function &emdash; and single_tag_title() &emdash; a function that’s very useful for tag archive pages.

I’m glad that my favorite blogging platform has finally implemented tags, although I wonder how truly useful it will be for people. Particularly in blogging tags often end up being superfluous; I think it’s because a blog’s tags are not collaborative, but often bloggers don’t have any experience tagging outside of collaborative systems and don’t really bother to think about whether they are using tags in a useful fashion.

Which actually makes me curious; do you, my gentle readers, find Tagamac’s tags useful? If you do (or don’t), please tell me about it. I know that when I’m trying to find old articles on Tagamac I often use the tags, which seems hopeful, but I’d be very interested to hear if they’re at all helpful to other people.

Plus if I get enough feedback perhaps I’ll be able to offer some informed opinions to the new-to-tagging WordPress crowd (instead of just opinions). Everyone and their mother seems to be sharing advice on how to implement tags into themes, but no one seems to be thinking about how best to tag a blog.

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.

Why Ma.gnolia? Because visiting del.icio.us is like getting slapped in the face by the color blue. This is my first venture into the world of social bookmarking, and I’d rather see pretty flowers than try the site that started it all.

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.

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.