I’m trying out the Mac-only GTD application OmniFocus at the recommendation of a few friends, and am liking it so far. While I tend to use Remember the Milk for most of my task management needs, it has not proved robust enough for complex project planning.

You can do just about anything you want in RTM, but certain types of planning and organizing are a bit awkward, and go beyond its intended usage as a to-do list (though, I must add, it remains one of the best web applications in existence). For example, it’s often helpful to see a project as a series of ordered steps, but RTM does not support task ordering or nesting.

I’ll put up a full review with recommendations once I feel more comfortable with my implementation of GTD with OmniFocus, but for now I’m still hunting for usage and optimization tips. While looking for a way to get SMS notifications (which I did not find), I came across this discussion on the OmniGroup forums, which raised a question I’ve never thought of before: How much should your GTD system interrupt you with reminders?

Since I use Outlook and Remember the Milk, I have several ways to ensure that I get reminders of important tasks and appointments. David Allen recommends only putting the “hard landscape” on your calendar - that is, only real appointments that you will actually keep should go on the calendar; tasks you can do more or less any time soon - as soon as possible - should be kept elsewhere so they don’t clutter the calendar.

I tend to date my Remember the Milk tasks with the time I should start them by, building in enough time so I can complete them by the date they’re actually due. Ideally I’d specify a start date and a completion date, but RTM only has one date field.

Of course, when certain tasks aren’t actually urgent, a problem quickly develops with this system: a large backlog of overdue tasks, few of which are really overdue. The ones that really are due get buried among the others, and the system loses its effectiveness. I get SMS reminders at the exact time I specify for each task, but this is useless if I can’t actually complete the task when I get the reminder.

This leads me to recall perhaps my best GTD insight yet: An organizational system is not a motivational system. Knowing what you should be doing is not the same as wanting to do it, much less actually getting it done. This occurred to me almost a year ago, but not until today did I see how my own GTD methodology fails to take its truth into consideration.

I’ve tried to compensate for this in RTM and Outlook by using invasive reminders - SMS messages sent to my phone, or popup reminders on my desktop PC. But it doesn’t really work for things I don’t want to do in the first place. For appointments that I have no choice but to keep, it works great - the “hard landscape of the day” is what reminders were meant for. They are intended only to remind, not to motivate.

In the aforementioned discussion thread on the OmniGroup forums, the creator of the thread suggests that OmniFocus build in more nagging reminders - completely configurable, of course - in order to remind him what he needs to be working on. The other forum members quickly denounce this suggestion, saying, in effect,

Instead, they say, you should review your system regularly and make a decision about what you should be working on. You don’t need nagging reminders - in fact, using such reminders (except for hard-landscape appointments) is a clear sign that your GTD system is not working.

This was a tough realization for me. Perhaps I should give up looking for ways to bug myself, and work on developing the habit of reviewing my tasks and projects more regularly.

OmniFocus is designed to give you complete control of what you’re looking at, with filters, a “focus” button that hides everything except the project you’re working on, saved views (called Perspectives), and more. It goes far beyond RTM’s Smart Lists feature, so if you want to see 10-minute tasks due yesterday in project X that you can do while on the phone (@phone), you can, and you can save this view - and create a keyboard shortcut for it - very easily.

The discussion thread contains a bit of argument about whether software should a) work the way users really work, or b) require the user to learn new, more effective behaviors. Most of the comments fall in the latter camp, arguing that software developers shouldn’t facilitate bad habits by adding unhelpful (if tempting) features such as nag-me reminders.

What do you think?