As teachers, we help students become comfortable with the discomfort of learning, so that they can engage new perspectives, gain experience discussing complex issues, and grow in their capacity as thinkers and writers. This work has become more difficult in a cultural moment saturated with fear. Fear drives book bans and curriculum censorship, with claims that such acts protect students from difficult ideas or information. Fear also impacts teachers, who may anticipate consequences for conversing with students about the many difficult issues threaded through literature and our students’ writing and lives—race, gender identity, suicide, poverty. Fear also prevents possibilities for dialogue and connection. In this Advanced Institute, we will come together to explore strategies for teaching difficult conversations in a divisive political moment and for communicating the value of this work to the public. Because of the additional labor this requires of educators, we will also consider how we can support ourselves, our students, and one another in this challenging time.