The catalyst for this self-study research was the performance of a sequence of poems at a colloquium for South African deans of education. The poems portray my interpretation of my students' stories of physically and emotionally painful experiences at the hands of their former teachers. My intention was to show how the creative possibilities of poetic language and poetic modes could enrich teacher education practice and research. However, while reading the poems, I was conscious of a palpable sense of distress building in the room. I began to wonder if I had made an awful mistake. Later, I questioned what I could or should have done differently, and, in this article, I offer an account of my efforts to learn from this painful poetry performance. I draw on the literary arts to combine vignette, poetry, and dialogue to inquire into my lived experience. Overall, the article demonstrates how extending my reflection through conversation with others allowed me to clearly see that my task as a teacher educator and educational researcher is not to avoid communicating heartbreaking stories in an emotionally powerful poetic format. Instead, it is to try to do so in emotionally supportive and educative ways. I offer my inquiry as an exemplar of how the literary arts can enrich teacher education practice and self-study research in creative ways to engage self-critically with social responsibilities.