A world with outsiders and insiders implies some kind of test for distinguishing between them. And the trouble with most tests for selecting elites is that there are two ways to pass them: to be good at what they try to measure, and to be good at hacking the test itself.
One way to tell whether a field has consistent standards is the overlap between the leading practitioners and the people who teach the subject in universities. At one end of the scale you have fields like math and physics.... At the bottom are business, literature, and the visual arts, where there's almost no overlap between the teachers and the leading practitioners. It's this end that gives rise to phrases like "those who can't do, teach."
It's kind of strange when you think about it, because lord-of-the-flies schools and bureaucratic companies are both the default. There are probably a lot of people who go from one to the other and never realize the whole world doesn't work this way.
The lives of the eminent become scheduled, and that's not good for thinking. One of the great advantages of being an outsider is long, uninterrupted blocks of time.
The very skill of insiders can be a weakness. Once someone is good at something, they tend to spend all their time doing that. This kind of focus is very valuable, actually. Much of the skill of experts is the ability to ignore false trails. But focus has drawbacks: you don't learn from other fields, and when a new approach arrives, you may be the last to notice.
As well as being more comfortable working on established lines, insiders generally have a vested interest in perpetuating them.
Responsibility is an occupational disease of eminence. In principle you could avoid it, just as in principle you could avoid getting fat as you get old, but few do. I sometimes suspect that responsibility is a trap and that the most virtuous route would be to shirk it, but regardless it's certainly constraining.
The word "try" is an especially valuable component. I disagree here with Yoda, who said there is no try. There is try. It implies there's no punishment if you fail. You're driven by curiosity instead of duty. Which means the wind of procrastination will be in your favor: instead of avoiding this work, this will be what you do as a way of avoiding other work.
But the best thing of all is when people call what you're doing inappropriate. I've been hearing this word all my life and I only recently realized that it is, in fact, the sound of the homing beacon. "Inappropriate" is the null criticism. It's merely the adjective form of "I don't like it."