so, i don't really believe in good and bad (although of course they are real in some senses); phenomena just happen. but my closest thing to having an orienting principle is something like pirsig's "quality". the closest thing to "should" is that we should follow our consciences, act truly, and this is quality. (as a side note, most of these things, like "should", just depend a lot on the context and have a lot of different aspects to their meaning. it's perfectly reasonable to say you should work hard, shouldn't hurt people, etc.)
but my question is, how does bootstrapping fit in? what if you're shy, and if you act as your true self, you don't get many people interacting with you. but having more social interactions facilitates your own growth. so you temporarily stray from your conscience. and then you come back and find that you have a deeper understanding of yourself.
i guess my best answer right now is that you should take a more direct approach of being your true self throughout, not using bootstrapping.
maybe the deeper problem comes because it's not so easy to act truly all the time. the brain is just molecules, and like any other robot, we're following the determinism of the universe, according to how we're set up.
any notions of "deciding" what to do are pretty fuzzy and look different from different perspectives. so there may be times when you use bootstrapping because you do, or something else that looks sort of like boostrapping, or maybe it's not clear in some senses, or from some "perspectives" (which themselves are just molecules going through some movements), what acting truly is. bootstrapping happens, and buddha breathes. there's a real breakdown between form and content.