After yesterday's post about my someday/maybe list, I decided to be a little more proactive about things. I dumped all of my current items into an org-mode file and assigned custom properties for estimated size, area of responsibility, and a future column for the action I want to take.
Using org-mode's column view, it looks a bit like this:

The columns are configured with the following settings, and I added properties for each column to make data entry quicker:
#+COLUMNS: %60ITEM(Details) %10AREA(Area) %8SIZE(Size) %8ACTION(Action) #+PROPERTY: AREA_ALL Personal Work FreeSoftware #+PROPERTY: ACTION_ALL Do Delegate Defer Delete #+PROPERTY: SIZE_ALL hours days weeks months years
I wanted a rough idea of how large tasks are, so I didn't try to be too accurate with the size column; using hours, days, weeks, months, and years gives me enough detail to decide on actions to take. I also assigned an area of responsibility (e.g. work, free software, etc) so they can be tied to larger goals.
Finally, I went through each item on the list and asked myself a couple of questions:
- Would I be okay if this thing never happened?
- If it does happen, do I want to be directly involved, or am I okay with just putting the idea out there?
- I if I am involved, would I be okay hiring someone to do some or most of the work?
- Do I want to do it all by myself?
These questions are similar to GTD's 4 D's: do it, delegate it, defer it, or delete it. If I wasn't sure about any of them, I left the "action" column blank (aka deferring it).
A lot of the list is still deferred, but it was a helpful first step and it eased some of the discomfort I'm feeling. Going forward, I want to make triaging my someday/maybe list part of a monthly review. Weekly feels a little too often, although that might change as the list gets smaller.