[jsharf]

The notion of a "deep enough stack to keep the pointers to those context handy" depends on the complexity of what you're learning. If the task at hand has a large enough memory demand, then you might find yourself "swapping" to external storage too frequently, and someone with even a slightly better working memory might not have to -- they'll probably be able to learn much faster.

That being said, this is an opportunity, not a problem -- if they learned something, they can probably explain the concept to you much more efficiently and help you learn as well. Some of the best learning resources online are informally written blogs :)