Good advice. Low-tech is the way to go when starting out, unless you’re completely familiar with the digital tool being used, like Outlook. Even if you’re convinced you’ll be taking an electronic direction, save the technology for a second learning curve, and focus on the method first.

This long comment just to suggest one thing : the important is the method, not the tool you are using. At the beginning it’s a little bit overwhelming to implement such a system on a new gizmo (iPhone and others). I always suggest to start with a pen and paper. When your system will be up and running you’ll be able to use new gizmos if you like.

In most cases, contexts are self-evident. “Get washer from hardware store” is obviously an errand. “Email Susan” is a computer task. The perceived complexity of context usually has to do with (a) not articulating in writing where you see yourself performing the action, or (b) thinking about the overall number of lists rather than the fact that only the list that matches the current context needs to be reviewed at any point in time. Occasionally more than one list is applicable (with a cell phone, @Calls and @Anywhere might be active lists), but sooner than later, you’ll get a clear sense of which lists you’re more likely to scan. For instance, I don’t do email on my phone, so even though I could technically put “Email Susan” on my @Anywhere list, I know that I wouldn’t be motivated to take action on it there, so I don’t put it on that list as an option.

But on the other hand I don’t want to be flooded with tasks so that the ratio of the timing “managing” that task is big compared to the task size itself.

I’m going to have to write a post about this phenomenon. I personally don’t believe that people spend more time managing tasks than doing them. I think that people are more self-conscious when managing tasks than when they’re executing them, so the perceived passage of time is heightened. As the saying goes, a watched pot never boils. Each phase of managing an individual project — collecting, clarifying, organizing and reviewing — should take less than a minute in more cases. It might take longer if the issue is more ambiguous, like clarifying precisely what to do about graduate school or moving to a better city (e.g., what does “better” mean?), but even if it takes 10 minutes to carry your thinking forward on those, the time spent is far less than trying to incubate an issue you haven’t fully articulated to yourself.

It seems there are problems with both extremes of large, chunkier tasks that are “worth” the effort to manage and a flood of small, no brainer, actionable tasks but that take more time to manage than they are worth.

The smaller tasks are more insidious distractions when dismissed as unworthy of tracking. It’s really not a matter of whether or not something is judged to be big or small so much as whether or not it has a claim on your attention. If an overdue library book has more of your attention than your next car payment, it’s probably because you know the car payment is consequential enough to get handled without much prodding. The paradox is that smaller items tend to require more effort to remember than big ones, and by keeping them only in your head, the effort needed to keep them conscious has to come from some of the bandwidth used to keep track of the big ones, creating undue anxiety. The consequences are complex, but the solution is simple. Track everything that has your attention without deliberating which things are “worthy.”

The two minute rule helps, but only seems to help if I’m in the right context for the task that I’m entering when I enter it.

True. The upshot of writing down out-of-context actions is that the next time you’re in the corresponding context and review that list, you’ll have one or more “cheap wins” to knock off without having to think about what to do next.

I am planning to use “Things” and sync to the iPhone to “take it with me” but I got stuck when it turned out they didn’t support tags on the mobile version so I’ve mostly been playing/practicing. Now that they are on the cusp of supporting tags on the iPhone version, I’ll try to make a serious commitment and hopefully come up with something that works productively.

I can’t comment on the iPhone. I had an iPod Touch, but didn’t find it as straightforward to use as a list manager as my Palm Centro. Good luck with it!

I am planning to use “Things” and sync to the iPhone to “take it with me” but I got stuck when it turned out they didn’t support tags on the mobile version so I’ve mostly been playing/practicing. Now that they are on the cusp of supporting tags on the iPhone version, I’ll try to make a serious commitment and hopefully come up with something that works productively.