Hannah Arendt has a particular notion of thinking that both is and is not (in her sense of the term) philosophical. While not guided by the search for meta principles, nor concerned with establishing logical systems, her notion of thinking as the examination of "whatever happens to come to pass," and its significance for saving our world from thoughtlessness, retains and is motivated by the fundamental "pathos" at the heart of philosophy--"wonder." In this paper, I consider the "limiting" and "enabling" sense in which Arendt invokes "wonder" for the possibility of thinking. I do so, in turn, to explore what the pathos of wonderment might offer education--an institution charged with cultivating "thinking" and, yet, constantly susceptible to the thoughtless trappings of technocratic jargon and the mechanical logic of assessment, learning processes and social reproduction. Can wonder--the very pathos of philosophy--cultivate a thinking that helps us retain an "unclouded attentiveness" to what is educational in education? Might wonder help us to overcome the thoughtlessness that dulls our attention to "what we do" to each other through education?