"Why is the practice of teaching worth putting at the centre of one's life?" Chris Higgins believes that this question must be properly addressed if people who become teachers are to become themselves--are to discover a way of simultaneously practicing their profession and "flourishing" as human beings. In this essay, the author aims to give an account of how Higgins addresses this question and to share his understanding of the question's fundamental relevance to teaching. At the same time, however, the author offers a critique of Higgins' central proposal: the use of "virtue ethics" and the associated idea of "receptivity to newness in new situations" as a way of avoiding factors that reduce teaching to moral obligation. The author maintains that a teacher "flourishes," not simply by being open to "new situations," but rather by being open to meeting, "self-critically," new situations. He argues that while this distinction seems subtle, it shifts the focus of a teacher's "deepest motivations" from "what" she perceives in a "new situation" to the act of her mindful self-reflexivity, an act that is nourished in her undertaking to find a personal resonance in the "new situation"--in the materials she must teach and in the boundaries she must abide by. The author articulates the distinction through Martin Buber's notion of "I-Thou" (Buber 2000), the idea that a person's "whole being" is found in her relation to herself as other. (Contains 5 notes.)