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Which Getting Things Done application to use has been on my mind lately, thanks in large part to the public release of OmniFocus which was closely followed by the iGTD 2 previews and my own Things screencast. With so many good-looking options either available or soon to be available, I’m sure that more people than I have been wondering which app will be right for them. Since I’ve had a chance to use almost all of them, I figured it would be nice to offer a quick general comparison of the available (and pending) options.

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.