Being in the moment, showing compassion, being non-judgmental, acknowledging deep emotional challenges without getting stuck: these are mindfulness characteristics important to us as teachers, yet not often included in teacher preparation. These concerns become magnified when we focus on difficult knowledge and thorny issues, like topics related to gender and race. Using a sociocultural framework, we address how mindfulness, heuristics, and other contemplative practices can be adopted to create safe, supporting, and healing spaces for such complex, often emotionally painful discussions. Participant narratives are used extensively to provide a voice to those marginalized or hurt. Drawing from these narratives and their experience in discussing thorny issues, we put forth possible solutions and interventions that can create spaces that encourage and support critical discourse through mindful practices. The development of a heuristic for discussing thorny issues whose characteristics can be adopted by interested teachers and educators to help frame and mediate this type of difficult discussion is an outcome of this research.