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I generally only use my "Waiting" context for those things that are routine/reliable enough that I don't usually need to further action or follow-up on them...

For instance, I'll clip order confirmation e-mails into the "Waiting" context so I can have a quick reference of tracking numbers and so forth, but I can generally expect that unless something unusual happens, the item is going to show up at the expected time and can be checked off in my regular review.

Likewise, I'll tend to drop in any "Waiting" items for projects that other people are responsible for managing/driving forward. In other words, if the ball and responsibility for the project is completely in the other person's court, it goes into a waiting context, as if they don't get back to me, it's really not my problem (perhaps they decided to drop the project and just didn't inform me, for instance).

On the other hand, if I'm dealing with things I need to follow-up on or take some action on later, I'll leave them in the appropriate context and just tack a start date onto them. This could be a person-based context (for regular project team members), or just a more general context like "Calls" or "Office" If the start date passes and I'm still waiting, that's my tickler to actually follow-up with the person, as the item will appear back on my radar on that date and time.

When things I'm waiting for do come to fruition before they've landed back on my radar, I generally just flip over the project mode and check them off from there, since that frequently involves some modification or at least review to the project tasks anyway.

I rarely put projects "On-Hold" ... I prefer to use start dates instead... I use this to represent either the actual start date of the project, or the date that I should follow-up to see if it's on-target to start. I suppose Someday/Maybe projects may eventually be useful to put on hold, but I don't have enough of those yet that it's really a problem with clutter.

I also have another context that I call "Simmering Pot" -- I use this to store actions that require some further thought to move forward... Usually ideas that occur to me that need further flushing out. These may become projects, or they may simply be checked off as non-viable, but ultimately I felt I needed a separate context that I could call up whenever I'm in "brainstorming" mode.