This article offers a reading of the philosophies of Emmanuel Levinas and Theravada Buddhism across and through their differences in order to rethink an education that is committed to ‘negative capability’ and the sensibility to uncertainty that this entails. In fleshing this out, I first explore Buddhist ideas of impermanence, suffering and non-self (anicca, dukkha, and anatta, respectively), known as the three marks of existence, from the perspective of Theravada Buddhism. I explore in particular vipassana meditation’s insistence on openness to the transient nature of experience and self, and the notion of ‘encounter’ that is implied therein. I then interweave this with Levinas’s notion of an ethics of alterity. I argue that taken in tandem, both provide the condition through which another kind of ethical sensibility can be developed—that is, one that is attuned to our encounters with the world. In conclusion, the article reflects on how this sensibility as ‘negative capability’ can re-inform an ethics of educational practices, which are by nature themselves necessarily involved with change and uncertainty.