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Since you're asking about this from a pure GTD perspective, I would comment to make sure that if you're attaching a "due" date to something that it's a 'hard' date. Not a 'I'd kinda-like-to' get it done date. But then the question becomes, how to prioritize? I know, prioritize is almost a bad word in GTD.

I come from a Franklin-Covey background, and it's been really hard for me to break the lettering/numbering habit. But what really didn't work for me was kind of the same thing that you're describing. I'd end my day with 10 things that were on my list for the day that didn't get done.

Granted, I don't have a lot of super-time sensitive things in OF. But I use a combo of flags and durations. I thought that the durations were kind of 'silly'. But when I'm stuck and I'm not sure what to do...I often look for a 3-5 minute task to get me rolling. I find that once I'm moving, momentum kicks in. I don't assign durations to everything, but I have several repeating things that I can look to to get me moving. And those are the things that durations are easy to plug in, because you do them often, you know. Plus, since it's repeating, you only enter it once.

Flags, I use to give me my 'do today' list. I don't feel as bad unflagging an item at the end of the day (for instance if it was a work task and I didn't get it done on a Friday, I'll unflag it and then re-evaluate on Monday) as I did when I stared at items that weren't accomplished on an FC daily list. Also, I never flag so many that I'm overwhelmed.

Others successfully use the next-action, which would be even more GTD, but I guess I like to be more in control.