Lucas: Regarding contexts
I've been using GTD for over a year and really, really like it. It's working far better than other approaches I'd tried in the past. I should probably go back and reread the book because I'm sure I've meandered a bit from a complete implementation.
My set of contexts is pretty small. For awhile, I tried @phone, @home, @laptop, @online, etc. It seemed overkill and cumbersome. I ended up with @work and @home. It was more of a logical context that made sense to me. There were things I would do during my work time and things I would do on my own time. The next action would start with a verb that would tell me what tool I needed: "Call Bill", "Look at www.somesite.com", "Pickup laundry". The way I worked the list was more by priority at the moment and it could be a call followed by a web site followed by sending an email. It was easier to see the list of actions for my work rather than scanning different location or tool contexts. That's just my experience and fits the way I work.
As for the Next Actions in contexts. I try to only have one Next Action for each project across all contexts. It's the thing that needs to be done to move the project forward and you stick in in the right context. That eliminates the possibility of doing actions out of order if you have multiple actions in different contexts.
Oh, I read a Merlin Mann idea on 43Folders that a Next Action always starts with a verb. That tip helped me create better actions: "Call", "Sketch", "List", "Find", ...
As for the Office Max errand, I'd put down "Go to Office Max (labels)" in my @Home context (yeah, I'm not really at home but it's a non-work task). My list might already have "Go to cleaners" or "Go to library (drop off CDs)". At some point, I'd head out the door and know I had three stops to make.
Again, this is just my way; your mileage may vary.
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