Unanticipated outcomes and adverse events are inevitable in surgical training and practice and tend to elicit complex emotional experiences, including regret. Navigating these experiences with support from mentors and peers is essential for surgeon well-being, a healthy surgical culture, and optimal patient care. Critical incident stress debriefing and metacognitive behavioral models offer tools senior surgeons can use to help junior surgical colleagues in the wake of unanticipated outcomes and adverse events.