OmniOutliner
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Stellar outlining program from OmniGroup (official page).
Here’s a simple file that contains the 12 months of the year with appropriate day items for calendering, planning, logging, or other purposes: Year.oo3.zip.
OmniOutliner and GTD
Over on the 43folders wiki there’s an article on OmniOutliner and how it can be used with GTD. My contribution is below. This is an older setup which isn’t quite what I have now settled on. (See OmniOutliner Revisited.)
Contexts and Projects
I went with a bit of a different approach, using "@" Contexts as the root level, then Projects. With auto A-Z sorting turned on, this enables me to sub-divide big projects into their proper subprojects (and associated actions) without too much nesting. Viz:
* @_inbox * @house * @computer * @office o website: make space on server + download out-of-date files o website: redo front page + read email from client * @stores * done * waiting
Using hoisting, and an open side drawer, I can view a single context list, or even a project’s, on its own, which helps when there are dozens of actions. I created an OmniOutliner template of my setup described here, though with more "canonical" contexts. Download here.
Wishlist: In-Progress indicator
One feature I wish OmniOutliner had was a third (actually fourth if you count the “none” option) status indicator to go with its checkboxes. On your to-do list, an item could be undone (unchecked), done (checked), or in-progress. I’m thinking an ellipsis “…” would work well, or (if you want to keep the checkbox metaphor), a small dot inside the box.
I submitted this as a feature request to Omni back before version 3 came out, so hopefully it will make it in some day.