Permaculture has a concept that it is the boundaries where interesting things happen - Where desirable life can be found. Between the forest and the meadow is where lies the life that may be desirable, whether fauna or flora.
I had labeled the two distinctions as destroyer/creators versus maintainers. I tear things down to create better replacements, whereas my partner is an excellent maintainer - As long as my new system is not too onerous, she is usually willing to keep it going, as I move on to the next process. And it seems that the transition from a small company to a larger one is also the transition from the independent to the more conventional minded, even though it contains its own traps (like having independents forced out - even from their own companies, or being strangled into oblivion by bean-counters, as it were).
Those who don't/did not do well in school may be in the independent group, more often than not. But then that misses other underlying reasons, like a few of my friends who had undiagnosed dyslexia.
I found a helpful guide to develop those analytical/independent thinking processes in Harry Browne's book How I Found Freedom In An Unfree World. https://www.nateliason.com/notes/freedom-unfree-world-harry-...
Although I have usually been attracted to conspiracy theory just to be at odds with the rest of mainstream thought, I recognize I do not practice enough critical thinking if said theory already conforms to an existing bias I may have - Another place for me to practice my mental strength!
Another item in HN's feed this morning is Connections - That series has been an invaluable cross-discipline introduction to so much thought and design of other creative independent types. https://news.ycombinator.com/item?id=25218056
Last, I agree with the concept of reading good autobiographies of interesting thinkers allows me to think some of the same thoughts they did...