This paper explores the concept of "Gelassenheit" as developed in the later thought of Martin Heidegger. It seeks to show the relevance of this to aspects of education, especially to the ways that teaching can be enhanced in order to do better justice both to the learners and to what is studied. Thinking in this way helps to overcome the dominance of representational thought, a kind of thinking that imposes barriers on the understanding and restrictions on how the world can come to be. In the end the thinking illustrated by "Gelassenheit" constitutes a more responsible and more responsive relationship to the truth. My paper provides examples of ways that this can enhance education. In the end, with a caveat, I revisit and re-examine aspects of Heidegger's work about which I think there is reason to be cautious. This is to encourage a degree of vigilance in relation to Heidegger's thought, but in a way that does not deny its powerful insights.