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Thanks everyone for the responses. I have to admit, though, after reading through them last night, I walked away even more confused.

Specifically the suggestion that contexts should be so general. Like assigning all of my graphic design work to @desk or @computer. 95% of everything I need to get done is at my @desk and @computer so that wouldn't help me at all.

I do like the idea of separate folders for home, work and freelance. That might help. But still, if there are @design tasks in work and in freelance, looking at a view with just the @design context wouldn't help me much.

And I do have David's audiobook. I feel like I need to go back and listen to it again.