If you're an OmniFocus user, you need to give two posts from J. Eddie Smith IV a read. He's sharing his setup and usage of the application, but the real essence of his message is that OmniFocus is just a tool. And like any tool, it's usage is only as good as the execution of the one yielding the tool.
I know that OmniFocus has a lot of power that I'm not using. But that's okay because I've (finally) reached a place in my life where I'm more concerned with doing the work instead of whether the work is organized in the absolutely most efficient manner possible. But I will also gradually improve my usage over time — it's impossible not to self-examine in this way.
Mr. Smith does a fantastic job of looking beyond due and start dates, flags, and contexts. He attempts to use OmniFocus to help him do the nearly impossible task of letting him know exactly what tasks are the most suitable at any given moment.
He eloquently describes the problem with any system, even one that is well organized:
But how do you decide what to do when 5 tasks are overdue, 14 are due now, and 34 are due in the next 24 hours? What about heart-palpating tasks that come due when there’s nothing you can do about them?
And the reality:
Ultimately, you still have to tell you what to do. And ideally, each successive action you take on will lie at the intersection of the three fundamental dimensions of productivity: time, priority, and context.
A big part of his solution is regular reviews. It hits my particular nail on the head:
Reviews also make it less likely that you’ll abuse your future self by setting meaningless due dates or stacking due dates on top of each other.
Due dates are my way of letting myself know I'd like to work on a task at a given point of time. But of course that emotion may be completely blown away when the time comes, the task gets ignored, as does my 'system'. All because I'd rather be working on something else in the moment.