Thread: Fear of OF/GTD
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Track things at the level of detail that you need to track to make sure they get done. You'll have to decide what that level of detail is for yourself. One of the factors I use to decide that for myself is how likely I am to be called away from a task, and how much context I'll need to get back to where I was before being interrupted, and to ensure that all the necessary steps are completed. If it is crucial that steps be carried out in a particular order, or with a particular timing, I'm going to put more detail into that project, because it will help guide me through the process. Many things may turn out to be cookie-cutter operations (paying the bills for regularly recurring expenses, for example) and can be neatly handled with repeating projects or Curt Clifton's Populate Template Placeholders scripts (available here) so you don't have a lot of extra typing to do. And there's nothing that says you have to track everything in OF, either, if you have something that does the job for you now. It might be reasonable to have a monthly "pay recurring bills" action that just reminds you to run your accounting package and cut all the checks there if it gives you the tools you need to track the payments.

Every month or quarter, take a little time to think about how well your tools served you, and where improvements would be welcome. You don't have to get your workflow, list of contexts/projects, organization, etc. perfect the first day. OmniFocus will let you evolve a system that works for you.