If you want to do history seriously, I think it makes sense to do it in academia. It's too easy to go off the rails otherwise.
More generally, there are two kinds of things we want to learn:
1) Purely intellectual areas, like math or programming. LWers have a comparative advantage here. But the uncomfortable truth is that most people who succeed in those areas had lots of schooling. (For example, Linus has a master's in CS, Google came out of a PhD project, and the idea of AI risk originated from academics like I.J. Good and Nick Bostrom.)
2) Areas with a physical or emotional component, like drawing, swimming, welding or public speaking. LWers have no comparative advantage here, and I strongly recommend everyone to take a "lowest common denominator" class. You'll be surprised how well it matches your ability.
The dichotomy is not that simple.
For example, in many areas of math it is of tremendous benefit to be able to internally visualize (with your "mind's eye") complicated structures and how they 'move' in relation to each other. Whether it's a skill or a ability, I've noticed some striking similarities to the internal visualizing skill needed in drawing:
To believably characterize a human figure in movement on a still paper that does not have ability to represent movement, it's helpful to see underneath the skin, to visualize all the muscles and bone...
LW has a problem. Openly or covertly, many posts here promote the idea that a rational person ought to be able to self-improve on their own. Some of it comes from Eliezer's refusal to attend college (and Luke dropping out of his bachelors, etc). Some of it comes from our concept of rationality, that all agents can be approximated as perfect utility maximizers with a bunch of nonessential bugs. Some of it is due to our psychological makeup and introversion. Some of it comes from trying to tackle hard problems that aren't well understood anywhere else. And some of it is just the plain old meme of heroism and forging your own way.