The two unteachable skills for self-bootstrapping insight:

1) You see that the world is not single-dimensional and black and white, but mullti-dimensional and gray.

If there's something that doesn't make sense to you right now, that implies some dimension or shade of gray you can't yet sense.

2) You meet disconfirming evidence with openness and curiosity.

When you see something surprising you don't lean back and say with a frown, "oh… that's interesting…" but instead lean in closer, with excitement, and say "oh! That's interesting!"

These two skills combined allow you to be antifragile; to grow from disconfirming evidence, instead of being worn down by it.