I had another look at the OP's post and he kind of reminds me of a student I had awhile ago. This person was very uncomfortable with uncertainty. He was very bright and worked very hard but if everything did not go exactly according to plan his performance suffered.
Things reached a head during navigation. His planning was over the top meticulous, but he putting a ridiculous amount of time into planning every flight. I eventually forced him out of his comfort zone with drastic measures. Just as he was starting his first leg I took his PLOG and threw it out the window. I then took his meticulously marked map and threw it in the baggage bay. I then gave him my rather tattered and unmarked map and told him to map read his way around our Navex and back to the home airport.
By the end of the flight he realized that navigation is not rocket science and the basics of time-speed-distance will get you where you want to go.