I first introduce three evolutionary waves of educational initiatives that have occurred over the last hundred years. Before identifying numerous postformal pedagogies—and showing how they align to postformal reasoning qualities—I discuss the educational theory of “postformalism” developed by Joe Kincheloe and Shirley Steinberg. I then introduce other leading educational innovators who are developing evolutionary approaches. Finally, I offer a more complex mapping of the relationships among the four evolutionary themes, the postformal qualities that relate to them and the diversity of postformal educational discourses. A major aim of the chapter is to map these different approaches, explore relationships among them and reflect this out into the broader education discourse.