The growing field of trauma-informed pedagogy recognizes that students impacted by trauma and grief require unique support in educational settings. Educators are often trained to approach students impacted by trauma with special care, yet little support exists for traumatized, grieving teachers. To address this disconnect, this chapter explores the impact of traumatic loss and grief on teachers. Drawing upon theories of grief, a variety of art works on loss, and the author's experiences with grieving while teaching, this chapter examines how grief impacts teacher identity, teacher perspectives on education, and the learning environment educators create for and with their students. The following questions are explored: How does power, fear, and vulnerability impact teacher identity and expressions of grief? How does the notion of teaching as a performance falter for grieving educators? How can teaching music and engaging with art influence and reflect the experience of grieving? An examination of the experience of grieving while teaching may yield new understandings about teacher identity and the roles of loss, love, empathy, and transformation in education.