I'll cautiously weigh in.
Based on my observations of fellow students back in the day, and those that I have instructed over the years, I would say that the risks of obsessive behaviour (not a great word but I can't seem to find better just now) are very real. I know of several who were unsuccessful as pilots for the simple reason that they could NOT let things go.
Yes, planning and checklists and routine are vital parts of preparing for and completing a flight safely. It is just as important to be able to prioritize. The aircraft will NOT stop while you recheck your plan 5 times, or do the checklist a few more times just to be sure.
As experience is gained and the flying gets more challenging it will become necessary to, at times, live with ambiguity. I hear the cries already! I didn't say accept ambiguity, just deal with it. Inevitably the aircraft will find a way to malfunction that isn't written down, or no matter how many times you ask the agency your talking to they just can't get you the weather. As pilot you must be able to keep functioning whether you are getting the things you want or not.
It is a fluid environment up there, and we must be able to adapt as well as plan.
"In preparing for battle I have always found that plans are useless, but planning is indispensable." - Dwight D. Eisenhower