At some point overthinking stuff can become a HUGE self-inflicted handicap.
If you become so excessively careful and caught up your own “logic” that you find yourself getting stuck and making little progress in moving forward, then I highly recommend employing this effective tactic to change things:
KNOCK IT OFF!
Give your gut the steering wheel more often.
And recognize making messes is a GOOD THING!
It means you are doing something including being willing to risk making mistakes.
It means believing in the most valuable of learning processes… piling up your own personal experiences vs. getting caught up in some prolonged form of mental masterbation.
If you find yourself playing devil’s advocate more than you find yourself actually trying new things or taking new risks, then you could be becoming a victim of your own cranal thinking.
Trying knocking it off and see what happens.