Consistent with the aims of this special issue, we present a systems perspective on self/identity, predicated on William James's classic distinction between I and Me, and use this perspective to explore conceptual relations between self/identity, motivation to learn, and self-regulated learning. We define the I self functionally in terms of the capacity for the conscious shifting and sustaining of awareness. The I is conceived of as that aspect of the self-system that affords the potential for the conscious and willful, rather than the non-conscious and automatic, motivation and regulation of behavior. We introduce contemplative education as a set of pedagogical practices designed to cultivate conscious awareness in an ethical-relational context in which the values of personal growth, learning, moral living, and caring for others are nurtured. We discuss the implications of contemplative education for the cultivation of conscious and willful forms of learning and living among students and educators alike.