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 OmniFocus 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.

That said, I have a handful of long-standing intentions that never seem to turn into action. Or, really, they’ll turn into a short spurt of action whenever I’m feeling particularly guilty or inspired about them, that quickly fizzles out as soon as something else comes up.

I think part of my problem is that I rarely set concrete goals for these things, only vague notions such as “exercise more” or “work on music” that do nothing to help me gauge whether I’m succeeding or failing. Another problem is that when I keep my personal plans private, I’m accountable to nobody but myself, and it’s all too easy to make excuses about why I did other things instead. So, I think I can beat both of these hang-ups by deciding on a handful of specific metrics and declaring them here in the open. Maybe I can shame myself into keeping on track.

It just so happens that now is one of the more ideal times for me to be refocusing my life. The entire second half of 2008 was impossibly busy for me, punctuated by frequent travel… at least, much more frequent than I’m used to. It looks like this summer may turn out the same way for me, and I’ve got another long trip planned for February, so if I want to establish some new habits, now is the time.

I don’t want to be unrealistic — the whole idea is to make these goals achievable — so I’m limiting it to five reasonable objectives. At the same time, I do want to stretch myself a little, so in addition to five modest goals each one will have a more challenging pair. If I hit the first target, I can feel pretty good about myself, but if I hit the second, even better.

Music

I have a life-long love of music… and a life-long habit of collecting musical instruments and projects, only to let them fall by the wayside. For ten years now (wow, has it really been that long?) I’ve dabbled in electronic music production, but have yet to really finish even one track. I’ve started plenty, but tend to lose interest or become otherwise distracted before any of them are finalized. OK, so it’s a hobby, and maybe I should be happy to just play around, but it would be nice to see something through. I’m going to try to put together a short album of techno and electro tracks, and if that goes well, a second collection of a few more free-form tracks.

Good: A five-track EP
Better: An additional three-track EP in a more adventurous style

Writing

It seems like I write a blog post every couple of months about how I need to write more blog posts. In November I said, “surely I can think of something interesting to post at least once a week.” It turns out, thinking of things to write about isn’t as hard as actually taking the time to write them. So I’m going to dial down the ambition a little bit and shoot for somewhere between one and two posts each month.

Good: At least fifteen posts this year
Better: At least twenty posts this year

Exercise

I’m not getting much of a workout sitting behind a desk for eight-plus hours a day. This is nothing new, but I think it’s starting to catch up with me. When I first moved to San Francisco, I lived at the top of a steep hill, which helped me get my heart rate up every day, but now I live in the flattest part of the city. I walk to work most days, but it hasn’t been enough to keep me from gaining weight in the past year. I’m still far from overweight, but if trends continue I may not be for long. Beyond that, it can’t be great for my health in other respects to be so out of shape.

I’ve never liked gyms, but several months ago Sharon & I got a stationary bike. In true San Francisco style, we found it on the curb outside our apartment. It’s pretty common here for people to leave unwanted items outside on the sidewalk for other people to claim. Usually, there’s a pretty good reason these things are unwanted, but this thing looked pretty clean and in good working condition, and it appeared out there in the time it took us to go out for brunch and come back, so we figured, hey, why not?

Since then, I have been mostly using it as an elaborate towel rack. It’s kind of ridiculous… as a form of exercise, it couldn’t really get any easier or more convenient. I can use it from the convenience of my home, and listen to music or a podcast while I cycle. I don’t need any gear other than what I already lucked upon, and there’s no need to coordinate with anyone else. Surely 25 to 45 minutes per day can’t be that hard.

Good: Average three hours per week on the stationary bike
Better: Average five hours per week on the stationary bike

Finance

Considering the times, we’re in pretty good shape. We’re not carrying any debt, we’re renting so there’s no mortgage to worry about, we’ve got relatively healthy long-term retirement accounts and a decent amount in savings. Still, I don’t feel like I’ve got a handle on where our spending is going, and we would eventually like to buy a house or a condo, so I feel like we could be saving more.

There are plenty of tools out there to help people get more of a grasp on their finances. There’s Quicken and the like, and in the past two or three years a number of web-based solutions have appeared. Each of these has tradeoffs, but I haven’t really taken the time to evaluate them fully. I think the first step in any long-term plan is to figure out where you are now, so I’ll take a look at all of the options to help me do that and try to get one set up. Once that’s done, I can try to develop a plan with Sharon for the next few years that will help us reach our goals, even in uncertain times.

Good: Set up and maintain a tool for tracking finances
Better: Create and stick to a monthly budget, including allocations for investment and philanthropy

Organization

Part of the reason I think I have such a hard time working on long-term goals — things that I think are personally important but that are not really essential in day-to-day living — is that I have a hard time juggling all of the things that I want to do with all of the things that I feel like I need to do. A few years ago I was introduced to David Allen’s “Getting Things Done” methodology the same way many geeks were, through Merlin Mann’s 43 Folders weblog. The approach appeals to me, and I’ve read the book a couple of times, but I still haven’t found a “trusted system” for capturing projects and actions that appeals to me. I tried the all-paper route for a while, but it felt cumbersome. I really need something that I can use from a computer and from my phone. Echoing what I said about financial planning software, there are a number of web-based and local software-based approaches to task tracking now, and with an iPhone I wouldn’t need to be at a computer to use either. It’s again just a matter of trying them out and choosing one that doesn’t feel like a burden. If I can get that sorted out, I’d like to get the apartment organized better, and the first step in that will be to get rid of the piles of crap that I don’t want, need, or use anymore.

Good: Choose a tool for GTD-style task and project tracking
Better: Sell, donate, or trash everything in the house that we don’t want

Keeping Tabs on My Progress

I know that setting goals is pretty meaningless if I’m not tracking metrics on a regular basis, so as an experiment I’ve set up an account on Daytum to try to record my progress. I’m not sure yet if the site will really fit well, but it’s a start, and since it’s public, it helps to keep me honest. I’ll also plan to check in here a few times this year to note how I’m doing. If it works well, maybe I’ll start to make a habit of doing this every year. And if it doesn’t… I suppose I’ll have to publicly shame myself here so that may be all the motivation I need.

Hey, well at least I can add a tick to the blog post count!