There is a basic conundrum that runs through human affairs: the more we try to help people to do things on their own - to become more autonomous - the more the goal seems to escape our well-intended efforts. There is some sort of contradiction between giving “outside-in" help to people to make “inside-out" changes. This problem is especially prominent in both education and development. Our task is to investigate some of the history of this problem in the hope that any source of light found in one field will illuminate the adjacent vineyard.