The aim of this article is to investigate how a contemplative orientation to teaching may facilitate wholeness for teachers and students through a portrait of Diana, a kindergarten teacher working in a contemplative elementary school. The portrait, one of three portraits from a larger study, illustrates three central features of contemplative teaching: compassion, integrity, and mindful awareness. These three central features develop internally within individual teachers and are animated and influenced externally through their role as teachers. The context of their teaching, relationships with students, parents, and colleagues, and pedagogical choices, in turn influence the three central features. The emphasis on wholeness, unity, and integration of a contemplative orientation to teaching moves us toward a view of teachers and students as beings with not only minds and heads but also hearts and bodies. Contemplative teaching offers educational communities a path toward transformational, holistic, and integrative learning and teaching.