Drawing on American pragmatism, this essay combines Eastern and Western thought to explore compassionate, spiritual, and creative listening in teaching and learning. I believe that such caring listening draws us out of ourselves into others in a way that awakens unknown possibilities that may call us into an unexpected destiny. I will tell the story of the Bodhisattva Kuan Yin as a teacher and ameliorator of suffering. Inspired by this ideal image, it is suggested that teachers should be self-eclipsing while being neither excessively self-sacrificing nor self-asserting in their caring, creative, and compassionate practice. The paradox is that for teachers and others in the caring callings, to care for others best requires we care for ourselves, but to care for ourselves, we must care for others. The turn to pragmatism will seek to justify this paradoxical position. It relies on the claim that personal identity, including our identity as teachers, is fluid rather than fixed and final. The identities of teachers and students are co-created and constantly evolving. Teachers value the psychic rewards of creative autonomy in the classroom, forming connections with students, and making a difference in their lives. Compassionate, spiritual, and creative listening supports these goals.