To make the situation worse, I was traveling for work at the time, 2,812 miles from home and my extra pair of specs. Luckily, I was in the second-least-horrible place in the world this could have happened: Washington DC. I grew up just outside the city, worked in it for six years, and spent most of my free time between June 1998, when I left school in Pittsburgh, and April 2005, when I moved to San Francisco, in the neighborhood where my hotel happened to be. I still know the city well enough that I was able to stumble my way around and find food for two more days without being able to read any of the street signs or storefronts until I was just about right on top of them. But it was not fun, especially when it came time to try to navigate the airports on my way home.

This is just the latest example of my notorious absent-mindedness. Just as with my eyesight, I have immense trouble keeping my attention focused without artificial aid. This plagues me in all sorts of different ways, from losing possessions, to chronic tardiness, to hobbies and projects that never really get off the ground. I’ve always been better at dreaming up ambitious plans than following through with them. I started writing this blog post over a month ago!

So, it was with complete earnestness and good intention that I published my personal objectives for 2009, and I made a good start on all of them, early in the year. As is often the case for New Year’s resolutions, I fell off quickly. I haven’t given up, though, I’ve just changed my approach.

I think it was a mistake to try to do all of them at once. Embarking on five projects at once is a great way to avoid focusing on any of them. I have to force myself to tackle one at a time.

The natural place to start is by getting myself organized. Without a good system for keeping track of all of the things that I want to do (or have to do), I tend to fall back on doing whatever occurs to me in the moment… and later stressing out about the things that I’ve forgotten during moments that I can’t do anything about them. As I mentioned in my last post, I’ve tried using systems based on paper or index cards for this before, but they never felt right. I really need the ability to sort, filter, and edit without having to spread things out across a table and keep a pile of blank cards on my person all the time.

I briefly tried some web-based applications, but they didn’t feel right either. I think it’s important to be able to capture ideas very quickly, at any time, with minimal interruption of my concentration. Requiring an internet connection—absent on the train and unreliable at other times—makes this impractical at times, and even when a fast connection is available, needing to go to my web browser, open a new tab, and load a site before being able to enter a new task is just enough of a context switch to make me lose my focus on what I’m doing.

So I quickly carved my choices down to the two most popular OS X tools: OmniFocus and Things. On their face, they are similar in more ways than they’re different. Both have a Mac application and and an iPhone companion that can sync with it. Both allow you to organize tasks around multiple dimensions (for example, the project it belongs to and the context you need to be in to do it). Both support repeating tasks, on-hold projects, deferred tasks and notes. Both have a quick entry window that can be called up with a keyboard shortcut to capture tasks without switching contexts. Both were built to support the GTD system, but also to be flexible enough to adapt to individual users. They each have devoted fans and a lot to recommend.

Things is a little newer, and has some great visual design. The user interface is simple and appealing, and it’s been promoted by its fans as the less complicated alternative. It supports flexible tagging of items, and has a very intuitive filter bar to limit your view to the items with the tags that apply right now. It’s also less expensive than OmniFocus.

OmniFocus, on the other hand, is a little more heavyweight, but also felt a little more stable and polished. It’s not quite as pretty as Things, but the UI feels more natural to me. It is a lot easier to use by keyboard, and it’s heritage as a descendant of outlining software makes it a really great way to organize thoughts that might start out as unstructured notes, jotted down in the middle of doing something else, and are later organized into multi-stage projects with smaller projects inside them. It may be more complex than Things, but the complexity mirrors the projects you’re using it to organize. It doesn’t need to be more complicated than you want it to be, but it doesn’t impose artificial simplicity on you either.

OmniFocus also has much better support for syncing across multiple computers than Things does. I switch between three different computers and an iPhone on a regular basis. OmniFocus handles syncing across the internet very well… maybe a little more slowly than I’d like, but with very few conflict problems and little effort required. For the most part, it “just works.” Things requires syncing to your phone over wi-fi, rather than syncing both the phone and the computer to an internet file server. This means you need to remember to sync your phone any time you make changes to your computer, or else you might find yourself at the grocery store with only half of your shopping list. The situation for syncing multiple computers is even worse: it requires use of a third-party syncing service such as Dropbox, and reports from users indicate that forgetting to close Things on one computer before opening it on another can result in a corrupt database. Ouch. Put those two problems together, and it makes it seem like syncing Things would require constant diligence and attention… in other words, I’d have to work around the software’s deficiencies rather than the other way around. That’s pretty much the opposite of the reason I’m interested in the software in the first place. Cultured Code, the company that makes Things, has said that better multi-computer syncing is their top priority for the next release, but I’ve learned in technology not to count your chickens before they hatch.

What’s more, during my trial of Things, I ran into a number of UI glitches and other bugs. It may look nicer in the pictures and screencasts, but OmniFocus felt more robust. This is not to disparage Things. It’s a new product and a few glitches are inevitable. But OmniFocus has the benefit of more maturity (though it’s only a couple of years old itself) and it’s still progressing pretty quickly. I had pretty much decided to buy a copy of Things when a 15% discount rolled into my RSS reader, courtesy of Daring Fireball. Sold!

A month later, I already feel like it’s helping, although I’m really only just getting started. One of the key insights in David Allen’s methodology is that the separation of capturing, processing, and acting on information helps to reduce overload. OmniFocus is really ideal for putting that into practice, and I realize now that the main problem with everything I’ve tried in the past is that they’ve only really covered capturing. Processing the information is too tedious with pencil and paper or basic to-do list applications, and it’s difficult to focus on the items that are currently relevant from one moment to the next.

Which isn’t to say that I feel totally in control yet. I still have much more that I want to do than I have the time and energy for, but what I’m hoping is that I can get better about juggling those things with the things that I need to do but don’t particular enjoy, and especially the things that I may think I need to do, but turn out not to be so important in the end.