How much planning and organizing do you really need to do? How much is enough? How much is too much?
Well, is your head empty? Then you’ve done enough. If something is still on your mind, you’ve got more to do. Most organizing and planning that people do is still lacking in the two critical factors for quieting the mind—What’s the outcome? What’s the next action?—with the answers placed in a system that our mind trusts we’ll utilize to review appropriately.
My mind is never really empty, but it is usually doing the more sophisticated job of making intuitive choices off my options, instead of trying to remember what they are. When it drops to the latter task, then I know I need to stop—then capture, clarify, organize, and reflect, to get back to appropriate engagement.
There is a point of diminishing returns from planning and organizing, where the payoff for the effort is not worth it. That point right before the return diminishes will be your most efficient and effective state. How do you find that point? You’ll probably need to over-organize, to know. Most people could use more erring on the over-organizing side of things, from my perspective.
But I organize for freedom, not constraint, and I’d recommend you use the same standard.