I see a lot of myself (when much, much younger) in Atlas in certain ways.
What he needs to understand is that he doesn't know shit. I mean he really needs to understand it, not spew forth a bunch of wannabe-zen bullshit logic like "I unremorsefully admit that I know very little and am learning every day" while continuing to be a pretentious fuckwit everywhere he goes. I mean he really needs to get it.
He needs to quit talking "bootstraps", when you can tell just by his YouTube videos that given his upbringing he has a very skewed definition of what "bootstraps" actually means. He needs to understand that by virtue of his situation, no matter what menial achievement he reaches it will never be a case of "well if I can do it, everyone can."
Atlas, I heartily recommend travel, since your parents seem affluent enough to let you put yourself in a position to make it happen once high school is done. You once mentioned that because of the "free market" you could get a broken leg set and cast in Asia for $200USD. I would definitely insist that you go there, or maybe somewhere like Ukraine, and see how "Doctors" live when they work for those prices, and perhaps check out the quality of the work and the sterile environments too.
But mostly travel because it's fatal to ignorance, which you are absolutely pouring with right now. Going to school in Chicago won't do it, you can likely find a mob of objectivist upper-middle-class douchebags where you can fit right in with, you need to get completely out of your comfort zone and experience some shit.
Finally, and this was the hard-learned lesson for me, you really may consider talking less and listening more. I've found that you occasionally learn (or at least develop a better understanding) by explaining a useful concept to someone who doesn't get it (I had a massive "oh shit" moment regarding pointers in C many many years ago, while trying to articulate my ill-founded understanding to someone who was utterly clueless), but for the most part you don't learn anything by talking.