Autodidact

For me, it was a hard won lesson to discover that my biggest obstacle to learning something on my own was the tendency to not start at the very beginning.

I absolutely agree, and unfortunately in my experience I ran into this as much in my formal education as my informal education. Not to knock my formal education, as I wasn't a great student in some ways and I think my curiosity was at times more intense than necessarily suited it, yet I found some of my troubles learning were that even formal education seems to struggle with determining where and how to start.

Take a classic example of a subject students struggle with like mathematics. For some students the issue is a matter of relating it to anything practical/real-world, however I also suspect for others the issue is both that and trying to grasp, without always knowing how to articulate it, the logical fundamentals that support and validate it. For many students it may be sufficient to begin with the basics of counting, adding, subtracting, and so on, but if you don't ground it both intellectually and practically, it's no surprise the further some students go the more difficulty they have finding it of any relevance.

It's similar with the subject of language imo. The practical part perhaps not as much, but establishing a foundation for why/how certain linguistic elements emerge and are arranged as they are, as well as how they continue to change, would I think better serve students along their start than a hollow, "This is just how it is" sort of approach that one may encounter in some early education/learning. Although perhaps I'm a very specific minority in this case, and some of the intellectual rationale for different subjects may be overkill for many to help them get going.