Lots of questions there and lots to consider. I guess the key for me is the note, I think it' s in Making it all Work but not sure that the question "is it actionable" during processing really is "is it actionable now".
My definition of now is within the next 3 months (a season) because of the work I do. But that alone allows me to put hundreds of projects into someday maybe that might otherwise clutter my current lists.
The two keys to handling large amounts stuff for me are:
1. Set a review time that is appropriate for the task I am putting on hold. So the template projects I have that are like checklists that I use to create a new one of that type are only reviewed once or twice a year. On hold projects like things I want to sew or knit may only get looked at once every 3 months. Things that could be done this season but are just out of scope for other reasons will get looked at every week during that season.
2. Defining contexts appropriately. I can handle hundreds of projects at once and feel good about it as long as any single context doesn't' have more than 20-25items in it. If a context gets beyond 25 next actions I know I need to either put some projects on hold or refine that context more accurately.
So for me that means that right now I have over 1000 projects of which 119 are currently active and being worked on and 56 are waiting for a future time to become active ( a tickler file for projects) while the rest are in true someday/maybe. I am also working with 41 separate contexts right now.
I schedule major reviews at the solstices and equinoxes. My big year end review is at the winter solstice and usually takes me about 10-12 hours over the course of a couple of days. I review every single thing on my lists and on hold in detail at this review. Plus I also do a lot of year-end filing and preparation for next year. Summer solstice review is about a 6 hour one where we go over what projects need to be done before winter. The equinox reviews are shorter, typically about 2-3 hours and are like simple course corrections. These longer reviews are where I really delve into the higher levels and re-think my life and projects, esp. the winter solstice one.
I use a list manager that makes it easy to set a review time appropriately for every single project and that really helps me.
Oogie McGuire - Mac, iPhone & Omnifocus
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Paonia, CO USA