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In our experience, when an action looks like it requires multiple contexts, it almost always means that the action hasn't really been broken down into concrete, discrete steps.

We're not saying that you should go too far down the rabbit hole of breaking tasks down into sub-tasks (“Well, in order to send that email I’ll have to fill in the ‘To’ field, then the ‘Subject’ field, then compose each paragraph…”), but in our experience, several small actions are quicker to accomplish than one big, complicated compound action.

This approach also lets you independently accomplish each part of the task and mark it as complete, rather than needing to leave the compound action sitting open on your lists until you've done all the things it actually represents.

Another downside to tagging is that it tends to alter the meaning of your context lists. Rather than a short list of actions that you know you can do, you end up with longer lists that are full of actions you may be able to do.

Those longer lists require you to spend time searching through your context list, deciding whether you can actually do each item. Time you spend doing that is time you aren't spending getting things done.

We understand that a lot of folks are comfortable with a "fuzzier" approach to their contexts/workflow, but when there's a conflict between what's comfortable and what's productive, we really want our software to err on the side of productivity.

Obviously, what's "productive" is a subjective judgement, and we're inevitably losing out on sales when we do this - there are other products that take a different approach to this issue. Having lots of options is actually a good thing, though! It's more important that folks be able to use a tool that works the way that they do than it is that the tool come from us.

Myself and the other support folks will be happy to help someone resolve any problems they're having applying a single-context approach to their workflow. Let us know which situations you're struggling with and we'll be happy to help. And if the lack of a multiple-contexts option means that OmniFocus isn't the right tool for you, we'll figure out another solution. One of our core values is that we shouldn't profit from selling tools people can't use or don't need.

Last edited by Brian; 2013-02-08 at 02:00 PM.. Reason: clarify the final 2 paragraphs