Nearly every teacher will experience loss and grief during their years in the classroom. And yet, too often the profession assumes that English language arts (ELA) teachers must hide the emotions that accompany loss. In this article the authors share strategies for supporting English teachers in making sense of their grieving experiences and thinking about how those grieving experiences might interplay with teaching literary texts in ELA classrooms. Based on research analyses, discussions with teachers, and the authors' own experiences in classrooms, they argue that acknowledging competing demands placed on teachers both empowers teachers to recognize the complex work they undertake and helps teachers to work toward healthier ways of teaching and being, especially during grief.