Medical education is known for its demanding structure, but the toll it takes on students and physicians is rarely addressed with the same intensity. Nearly 30% of medical students experience depression, and rates of suicidal ideation are alarmingly high—three times greater than their same-age peers. Residents and attending physicians face similar challenges, often without access to the care and support they need. Dr. Jenny Wei and third-year medical student Sanila Math join the conversation with Austen to explore the culture of rigidity in medicine—from its historical roots to its present-day consequences—across every stage of training. Together, they reflect on the weight of burnout and the importance of questioning systems that no longer serve doctors' well-being.