This is the biggest problem I have with GTD. And I'm sure it relates to habits that I simply do not have, and not only do I not have them, I don't want them! I am proudly in a situation where anything I need to do I can do wherever I want to. As a Software Engineer I am quite well equipped to do my job wherever I want to do it. And things like shopping or errands don't work well with concrete contexts either because frankly, I often find myself buying online or shopping around. I don't log on to Amazon.com every day and then see if there's something to buy. I log on because I want to buy something.
I have, however, begun recently a new purpose for contexts. Instead of thinking about places, or people as is commonly the example, I am thinking about *WHY* I am doing things. I find this is far more "honest" when I review a task I added to my inbox. For every thing I decide I need to do, I have a motivation, and to my surprise I found it relatively easy to categorize these motivations down to about 10 categories. Some of those categories are sub-categories of more obvious ones. The tree has three main roots: Work, Family, Myself. Under Family I have my primary role responsibilities as a father, accountant, husband. Under my self, I have my personal timeless goals, which are mainly my hobbies, Gaming, Photography, Self-improvement, etc. And under work, I replicated my roles there as well. I do work in multiple sub-departments so I use a context for each of those. I also use the root contexts for more general tasks, such as tasks I must complete for HR at work, for example. Though I could make a new context, I don't want to clutter up my tree with a bunch of contexts I rarely concern myself with.
Now, I feel much, much better about this organization for the concept of contexts vs. actual places. Though I still face some challenges in applying the tools, OF or even alternatives to this system. For example, the location-based context listings in OF for iPhone is effectively useless. I have no thought-free mechanism to decide what set of tasks I ought to be focused on. But my lax schedule of availability at work coupled with my highly centralized "living range" (I don't have to travel far from home to do anything I must do) it never really gave me much help anyway. I mean, my office is 5 miles from my home, and due to the inaccuracy of GPS on the iPhone I frequently had the location service telling me I needed to be working on Home tasks at the office :)
What has happened, though, I think is interesting. Instead of my location driving which tasks I want to do, the opposite happens. The combination of due dates, flags for priority items, and my personal prioritization of Family -> Work -> Self actually drives where I will be for any given time period. If I have a lot of priority items in the work context, I'll schedule my day to be at the office, or at least, somewhere where I can focus on work. If I have urgent family matters, I will simply deal with them, wherever they must be dealt with, and spend little or no time at the office.
I realize not everyone works this way, as most people seem to have fairly fixed schedules and locations, so I don't expect there to be tools designed around my personal habits or needs. That said, OF has been mostly helpful. I have the most struggle trying to come up with an effective listing of what's next. I am currently most interested to know what is due soon, and what have I decided I really want to get done (that's what I use flags for). Then I want to see them for all contexts, ordered by my prioritization of contexts. That actually almost works. I can't figure out any way to make a perspective that will do "Due Soon and Flagged" there is only a choice for "Due and Flagged" or whatever, and that shows me things that aren't due for a very long time, and I'm definitely not concerned about those things on a daily basis. However, while on OF for Mac I can select a context to filter for a priority area of interest to me at the moment, I can't do the same thing in the iPhone. I get a single listing with list dividers for contexts, and it's up to me to scan through and find where I want to be looking.
Besides the difference in applying contexts, I use a single catch-all SAL, projects for any well defined set of tasks that I have (some are really goals but I believe I can complete the goal so it gets a project) and I make heavy use of subtasks, usually in sequence mode, especially with work projects as I tend to outline the entire project as I see it, and make adjustments as time goes by, so I'll often have several levels deep of subtasks. This is the #1 reason I continue to use OmniFocus actually, the ability to be an outliner and task manager at the same time is nice.
There is one last function that I sort of wish I could more effectively use OF for, especially in the mobile context, which is information gathering. Right now I'm trying to use EverNote. But frankly, it's a whole gaggle of low quality software with more bugs than I'm comfortable with, and I'm not a huge fan of cloud storage of such private data anyway. I do like the basic functionality like being able to clip web pages into synchronized storage copies, as well as the tagging/searching functions. I could live without the OCR even though that's a nice touch. I'd really like to see OF come up with some feature enhancements that would make it practical to do this sort of notekeeping alongside my task tracking, as there is almost always an affinity between information I care about keeping and the tasks I need to complete.
So, at any rate, I am wondering if anyone else has similar takes on the use of contexts and has found, perhaps, more effective methods of applying OmniFocus to a system like this.