Do you want to manage your tasks and open-loops/projects easily and automatically? Do you want the ease of use of Kinkless GTD with the reliability of a commercial application? Well, so did I. This is what prompted me to finally settle on transforming Microsoft Entourage into the ultimate personal productivity system. This is the first entry in the series, so read along, and keep coming back to find out how you can work Entourage to your best advantage.

I started out with the Getting Things Done methodology about two years ago. I was working through graduate school, as was my wife (she still is, I’ve got my degree), and I was swimming in too many things to do and not enough time to do it. Prompted by the numerous enthusiastic reports of David Allen’s book on some blogs I frequented, I jumped on the bandwagon. I read the book, loved the approach, and have been valiantly striving to become a ninja-grade practitioner of GTD ever since.

But see, I’m an efficiency wonk, and a major geek, so I couldn’t just do GTD, I had to find a system that would let me do GTD better! I tried some note taking software, index cards, notepads, outliners, wikis and full blown web applications of all sorts. I’m a geek and a productivity/efficiency wonk, so I was happy to do it.

Finally, after months of experimentation and getting on and then falling off the GTD wagon, I became a Kinkless GTD (KGTD) user.

Kinkless GTD has much to offer. Because it has the incomparable OmniOutliner Pro, It’s efficient, easy on the eyes, quick to enter data, and very extensible since it’s entirely comprised of AppleScripts. As a user, I spent no small amount of time extending what KGTD could do, and making it work better with Apple’s Mail program, export contextual tasks to my iPod, and more.

But as I fiddled and toyed with the system, I became disenchanted. While the base KGTD outline worked great, its interface with the rest of my workflow was, for lack of a better word, broken. This wasn’t Kinkless’ fault at all! The problems were resident in iCal’s poor handling of date stamps, thus rendering Palm synchronization (Clie sync, in my case) useless. Mail’s AppleScript dictionary, while robust, is broken, and renders many common tasks entirely impossible, including such necessities as linking an email to a task in a fashion that will withstand moving the email from one folder to another.

And as for Kinkless itself, it was just AppleScript, and that was a failing. If I forgot to press “Sync” in the toolbar every day, it didn’t update. If I marked a task with a date in one place, it might get another date from another location in the document. KGTD is good, but it isn’t bulletproof, and worrying about whether my task and project lists (the lifeblood of my peace of mind) would survive the next Sync was not contributing to a mind like water. And isn’t that the whole point of the GTD methodology?

So, I went back to the drawing board, but more knowledgeable about what I wanted or needed from a task manager. I came up with a simple list of requirements:

• Easy and ubiquitous entry of new information via LaunchBar, Quicksilver, or darn near anything else. I am hopeless addicted to the “Send to KGTD” syntax (which I extended in my own scripts), and I simply could not live without it.

• Able to categorize my tasks based on two axes: Context and Projects. While The David may be content with a separate project and task list, having the ability to view my tasks both by context and by project cuts half an hour out of my review process.

• Integration with email. I have set up a GMail account which creates tasks. If I’m away from my computer, I can send it a task, and it pops right into my task list. (Thanks to the Mail to KGTD script.) Same goes for an email that requires action; I want to send it to my task inbox or to a project, not let it clutter up my inbox.

• Portability, on either an iPod or my Clie. I need to have my tasks with me when I’m out and about. Then I can take use of those precious ten minutes of slack time when I arrive early for a meeting, and can take a couple calls. Furthermore, on the portable device, context must be maintained, or else I’ll be swimming in tasks.

As I looked over this list, I thought of software that could handle it. There were the usual crop of wikis and other hacks. There was the excellent Ruby on Rails application, Tracks. There was even one fellow who hacked GTD into his GMail account. But none of these had all the key features I was looking for.

And then I thought, “Why not Microsoft Entourage?”

Why Entourage? Well, because it handles categories as well as projects, thus keeping everything nicely in line. It also has a phenomenal AppleScript dictionary, which was well up to the task of replicating the Send to KGTD functionality I craved.

As I poked around in Entourage’s inner workings, I found that the program, bolstered by recent updates, had even more to offer. It is Spotlight searchable; it shares its schedule and contacts with Apple’s Address Book and iCal programs, thus enabling me to keep using other programs that rely on those data-stores; it syncs effortlessly with my Clie, maintaining categories with aplomb (and there’s tools to sync to the iPod as well); and its use of custom views and categories makes it easy to slice its information into just what I want to see at any particular time – the ultimate goal of the context-based GTD system.

Entourage also has its warts, it’s true. Its Project Center appears to be the answer to all of a GTD user’s dreams – a single repository for emails, tasks, files and notes related to a given responsibility – but it’s kind of kludgy in some ways, especially when it comes to creating projects. (A three step wizard is the only way.) But then, couldn’t I AppleScript a way around that limitation?

It turns out that I could, and I have started to do so. The results have been incredible. I have full confidence in my system and am spending less time than ever fidding with its workings. While I’m certainly spending some time scripting and extending the functionality of my system, the basics are all built right into Entourage, and are therefore well supported by everything else that supports Entourage.

So, for the next few days, I’ll be posting a series of blog posts, and putting up a few scripts (in early beta, at best, but don’t worry, none will harm your data — I made damn sure of that!), about how you can Un-Kink Entourage (a homage to Kinkless GTD, I assure you, and not poking fun), and turn it into a superb storehouse for your actions and open loops and even for the other random files which end up getting in the way.

This is all built on 10+ years of AppleScripting know-how, a deep appreciation for the finer points of organization, and a firm desire to put the best of Kinkless GTD into a more robust and automatic system. I welcome your comments and questions throughout, and will try to answer them directly in the comments section, but may keep some as grist for additional articles in this series.

And yes, I know, The David has his own guide to implementing GTD in Microsoft Entourage. But his costs $10 and mine’s free and comes with oodles of software. (Now might also be a good time to mention that I’m not associated with David Allen, the Getting Things Done book or concept, or anything else — I’m just an enthusiastic user.)

If you’re feeling adventurous, dust off that copy of Entourage, update it to the latest version, and join me on this wild ride to turn the corporate behemoth into a lovely and efficient task manager.

Next article in this series: Un-Kinking Entourage Part 1: The Basics