Lurking in the shadows of education history are networks of human interaction, transcultural encounters, forms of global connection, and dispersed sites of cultural teaching and learning that are barely visible in the master narratives of education history. Who would have thought a half-century ago that we would become witnesses and participants in an increasingly interconnected world, bound together by global systems of commerce, transnational structures of communication, tsunami-proportion migratory flows, and ever more complex and puzzling transcultural encounters? Who could have imagined that sites of teaching and learning could become geographically unbound, disentangled from life in face-to-face communities, and the traditional boundaries of nation-state and imperial empire? How might historians of education take account of a world of unrelenting pluralisms, complex border crossings, and de-territorialized networks of association that have evolved in the last half century? The work of collecting stories, stockpiling memories, creating archives, and accumulating information is important work at this time--not only to shine a light on living history, but also to reveal processes of social change and features of the recent past that might be otherwise ignored or lost in history and to historians. This article presents a meditation on the lives and consciousness of two unconventional living educators who have struggled to recast the contours of what might be imaginable, knowable, and doable in education. (Contains 20 footnotes.)