I took "looping" and "incapacity" to mean not taking a leap. Growth usually happens outside your comfort zone. Remove the safety net and ask, 'what's the worst that could happen?'
Yeah, "incapacity" is the wrong term, since more learning should never decrease your capacity to do something.
He's against the overlearning of a skill in a classroom, especially since you won't really learn how to do most things until you close the books and just go do it.