PROBLEM: Failure is a powerful teacher but an emotionally stressful experience. Before residency, when failure in clinical training is inevitable, medical students should learn to talk about and cope with failure. However, medical school curricula rarely include this topic, and physicians seldom share their mistakes and failures with trainees. This report describes and evaluates a workshop on dealing with failure in medicine. APPROACH: Two attending surgical consultants and a life coach facilitated the workshop between February 2021 and February 2022, which consisted of different educational approaches, such as presentations, small group discussions, and journal clubs. The sessions aimed to enable medical learners to identify and analyze actual and potential failure events in everyday clinical practice and learn from them, disclose and communicate medical failures and "speak up," reflect on failure and develop coping strategies, and understand the moderating role of fear of failure. OUTCOMES: Thirty medical students participated in the workshop. Dealing with failure in a productive manner was the medical learners' key learning objective and anticipated takeaway from the workshop. After the workshop, 19 of the 30 participants anonymously completed the standard university evaluation form. The medical students gave the workshop a mean (SD) rating of 8.59 (0.98) on a Likert scale ranging from 1 to 10. They felt better prepared to approach future challenges in a constructive manner after being equipped with strategies to deal with failure. Listening to the failure experiences of faculty and peers in a safe environment helped them accept that failure is inevitable. NEXT STEPS: The findings suggest that medical students appreciated a safe environment to discuss failure. By promoting a safe learning environment early in the medical career, medical schools could make an important contribution to reducing the stigma of failure and eliminating the shame and blame culture, thus contributing to students' well-being.