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Great article!
I've been playing around with something similar, but arranging months(ish) so they build on each other, similar to how weightlifters arrange their blocks of training.
A Weightlifter might do:
General fitness -> Strength Training -> Sport Specific Prep -> Competition
A knowledge worker might do:
Build fundamental habits/systems to support work -> Push to improve skill -> Redline work output -> Deadline (or not)
I wrote more about it here: https://jamesstuber.com/periodization/
Your pentathlons are perfect for the first phase. By the end of the two weeks hitting sleep, exercise, nutrition, planning, and MIW targets is easy. Then you can push on new things while your habits/systems just keep humming along.
I half-assed a plan like this last quarter but will execute this quarter and report results.