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I’ve been contemplating switching from Things (the task-list app that I’ve been using for years now) to OmniFocus. Downloaded and tried out the trial version of OF. Seems interesting so far, but there are various features that I wasn’t quite sure how best to use, so I went looking for more info, and found that (as seems to be usual with task-list apps) the answer seems to be “use them however works best for you.”

So if I want to switch, I have to not just change apps, but also come up with a new paradigm for managing my tasks. Insert standard joke about task-management people spending more time figuring out how to use task-management tools than actually doing tasks.

But in this particular case, coming up with a new paradigm may not be a bad thing, because my old paradigms aren’t really working for me.

So I’m vaguely musing about how I want to manage tasks. I think the core issue is that I have several different kinds of tasks. The rest of this post is me musing about those different categories; I’m not going to come to any conclusions here about how best to do things.

• The vast majority of my tasks are things that don’t have deadlines; they’re things that I definitely want to do, and would ideally like to do soonish, but that I could do pretty much any time in the next year or two, or even put off indefinitely, and nobody but me would be affected.
• Some tasks are similar to the above except that if I wait too long, the opportunity will go away. For example, seeing a movie before it leaves the theatres. I guess making doctor and optometrist appointments is kind of in this category—there’s more or less a time limit, but it’s not immediately obvious what that limit is, and anyway it’s not in the immediate future. Putting up pretty lights outside my house is another one—the earlier in December I do this, the longer they’ll be up before I feel like I have to take them down to avoid annoying the neighbors.
• Some tasks are part of ongoing big projects; the task for any given day is to make incremental progress (and each day’s version of the task is essentially the same as every other day’s version of the task). Examples: do a Duolingo lesson, label 100 photos, read some of whatever book(s) I’m reading, etc. I want a new instance of each of these tasks to appear every day, but if I fail to do one on a given day, it’s not a big deal, I just delete that instance.
• Some tasks are adulting/chores that I should do every week or two: laundry, dishes, grocery shopping, taking out trash, etc.
• Some tasks are important financial things that have real deadlines but are fairly quick and easy to do, like paying my credit-card bill and phone bill each month, or paying my property taxes each year. But even these are things that I’m happier if I do before the deadline, but if they come up on my task list before the deadline, I see that the deadline isn’t immediate and I put off doing them. (I recognize that no task-management tool can solve the fundamental problem of my procrastination and avoidance behaviors.)
• Some tasks are things that have deadlines but that are not quick and easy to do, like doing my taxes or preparing to vote. Those are things where there’s no obvious specific starting date, but the longer I wait to start, the harder and more rushed the process is going to be. For this kind of thing, I probably ought to pick a starting date well ahead of time, and have nicely defined subtasks due on particular days along the way. (I feel like most of the task-management systems I’ve tried don’t handle this kind of time-limited ongoing task well, or at least I don’t know how to use them to handle it well. A project-management system might be more useful for this kind of thing, but those kinds of apps tend to feel to me like too big a tool for my one-person-project purposes.)
• Some tasks are more important than others. Sorting by priority is useful, though of course sometimes I would rather do the easy or fun tasks than the important ones.
• Some tasks are easier than others. I should probably be better about tagging stuff that won’t take me much time to do.
• Some of my tasks are of the form “Decide whether I want to do x” or “Decide which of x, y, or z I want to do” or “Figure out how to approach doing x.” Those are very vague and ill-defined tasks, and I often don’t do them because I don’t know how to start. Probably breaking them up into subtasks would help.
• A few tasks are things that I kind of vaguely think might be interesting or useful to do at some far-distant future time. I’m fine with just tossing those in a future-tasks bucket and never looking at them again.

There are probably other categories too, but I think that list covers most of my use cases. Maybe the next task on my list should be figuring out how best to handle each of those categories, either in OmniFocus or in Things.