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I found this useful. I already believe that plans are important, but going through your plan made me realize some useful tactics ("Have someone else understand the importance of this in case I die").

I suspect that to convince people that plans are useful you will need to address the broader philosophical systems that make one believe that plans are or are not useful. These systems seem to hinge on the questions: 1) Can we control the future? 2) Can we predict the future? 3) Do we need to predict the future to shape it? This view is broader than Thiel's 2x2 matrix. Effectuation claims that you can control the future and thus don't need to predict. Fail faster startup mentality (Lean Startup?) claims that you can predict to a limited extent. Nicholas Nassim Taleb claims that you don't need to predict and you can't, but you can play the odds by becoming antifragile.

A naive view of plans sees them as fixed. I suspect you need to address this as well and argue why Eisenhower was wrong when he said "Plans are worthless, but planning is everything". I further think you need to address Tempo.