In this paper, the author outlines what No Child Left Behind policy might mean first in personal then in philosophical terms. First, the author will trace a bit of Obama's own educational development: how he was first set on a personal educational journey and how, proceeding along with that journey, he eventually came to successfully elicit "us" to travel along with him on a similar, collective journey as a democratic people. Yet as a people, Americans clearly have only so far taken small steps along that journey since Obama's election. Americans need a clearer vision of where it is they should be going than Obama himself has so far been able to provide. So, second, he will begin to trace some of the philosophical roots of Obama's personal journey. (Contains 23 footnotes.)