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[An update in the comments below. This template makes the comments too unobtrusive, I think…]
I’ve noticed that System One seems to want to do things all in one motion. It wants the accomplishment of every goal to be as simple as extending your arm and hand to grasp a cup. Also, desire and “how,” ends and means, are intertwined: System One often does not make a distinction between X and “how to get X.” There’s just “Y,” which mixes those two things together.
If you’re bumping up against the seeming limitations of reality, I’ve found it tremendously helpful to explicitly split out “goal” and “planning.” I actually don’t even think about a single explicit GOAL. I simply have “goal time” and “planning time.” During goal time I only explore what I really want. During planning time I only explore how to get it. I can switch back and forth as many times as I want, but I have to spend at least six minutes before each switch. (I use six minutes because 6*5*2 = 60 minutes and then two sets of tally marks is one hour.)
For a single, broad, “goal-ish context,” like, I don’t know, fun+money+relationships (it should be bottom-up organic), I keep separate timesheets for goal time and planning time, as well as scratch paper per section, and some card stock for dividers and stiffness, all stapled together into a single packet.
I have a third section for “doing,” but I haven’t used it that much. If you spend time on “goals” and “planning” you may have some strong, unpleasant emotions for five minutes to 48 hours, depending on difficulty level. But then you might find yourself spontaneously and effortlessly springing into action.
Akrasia is failure of the imagination, not failure of the will. If I feel like I need to force myself to do anything, beyond some simple, painless behaviorism and bookkeeping, that sets off a blaring klaxon and flashing red lights that something’s gone horribly, horribly, horribly wrong. And I don’t stop messing around until the need for will goes way, way down to acceptably minimal levels. I try to use nearly 100% of my will to obviate the need for will. That scales.