You really only escape the ceiling going into business for yourself. And there probably has never been a time where it's easier to go into business than the last decade, because of the relatively low cost and high reward of developing software. Maybe that's why programmers are often restless, because the path to wealth seems close at hand (even when it's much harder than it seems, and requires many more skills than just programming).

Tu quoque: the "my boss doesn't understand" problem in companies basically comes from people working for people with lower IQ than them. It's not a skillset gap, it's a pattern-recognition gap.

In the military, the best soldiers become officers, and the best officers become generals—even though these are all different skill-sets—because it's more important to have a good general than to have a good soldier, and so if you could, theoretically, do both tasks well, then the military's comparative advantage in allocating your brainpower is to make you a general.

In tech, we see a "career track" of engineers that attempts to be a meritocracy, with the engineering leads and fellows being the guys who have been there the longest—but that's more like the NCO track of the military, valuing experience for the job they're doing, but not the raw brainpower and tenacity to do jobs well generally. Management, meanwhile, is not-at-all a meritocracy; managers hire from outside based on credentialism, and engineers are "pushed into" management based on credence from fellow devs (the same thing you get from being a battle-tested NCO), rather than being "pulled in" by an actual need.

The best gift I was ever given was to grow up on a farm. I'm doing way better than my peers.

The 1% are living in a way that will last longer than they will, on a scale that the rest of us won't achieve in our lifetimes. That's okay, certainly, but to pretend like there's no reason to work towards the 1% is silly.