How do we encourage Heidegger's notion of originary thinking in education, and indeed how should one engage with thinking at all? In this response, I consider the challenge that Heidegger lays down for speculation that refers certainty to the unknown. In my answer to the contributors of this special issue, I highlight the fact that all of us are compelled to depart from Heidegger at some stage but, at the same time, to carry vestiges of his meditative and exploratory thought with us as we start anew. Heidegger thus recommends that speculative thinking, and its dark participation with mystery, be honoured generally, in both educational contexts and in reply to others. Whether student or teacher, writer or interlocutor, one is rendered vulnerable in the face of that overwhelming call to think without a prescribed horizon, and I set out to explore some of my thinking as I respond to the deep creativity of the contributors' works.