I’m finally able to give a run to your idea of flags on maintenance tasks alongside the Flagged or Due context view. It seems like a very neat way of combining the views. I’ll give it a week or so to see how it runs …

- Kourosh

I guess I should go and actually do something now that I’ve spent a fair chunk of my day organising myself.

However, I tend to confine setting future start dates to those actions that either can’t be done at all until a future date, or those I’ve consciously put off until later (low priority things that I don’t want to think about). I’m fairly selective about what I apply start dates to: I have to be sure I don’t want that item on my radar before the start date or at least my next weekly review.

I most commonly use start dates for single actions, which I have a lot of, since I use Omnifocus for managing everything from writing a book to taking out the garbage. Actual projects are more likely to just get put on hold and then picked up during my next weekly review unless they actually do have a concrete start date.

However, I’ve also made much more judicious use of contexts in order to keep the lists smaller during my daily “tactical” review and allow me to keep a better focus on what’s important. For example, my “Office” context used to get massive, since I threw in everything I could logically do while sitting at my desk. I’ve since refined that into “frame-of-mind” areas, which are particularly useful for lower-priority actions that I’m only going to do when I’m in those modes. For instance, I have contexts such as “Leisure” for things like books I want to read, movies I want to see, etc, and “Research” for things I want to read up on, new software I want to check out, etc. These don’t get checked at all during my daily review, since I’m not going to find any items in there that would be important enough to “force” me into those contexts — they’re contexts I’m going to specifically visit only when I’m in the appropriate “mode.”

The final key here is the sorting and reorganization that I do in planning mode during my weekly review. Reorganizing the items in my single-action buckets and reorganizing my projects sets the order in which the items appear in my actual contexts. Since each context is in descending order by priority and I can only do so much in a day, I simply work through each context until I’ve flagged a realistic number of items and then ignore the rest.