Burnout is a leading issue in the United States healthcare system today, afflicting approximately 50% of physicians. It is characterized by emotional depletion and loss of energy, a sense of depersonalization, and a reduced sense of individual accomplishment, resulting in withdrawal from occupation. While often regarded as a personal issue, it is clear that burnout arises from organizational factors and therefore, warrants organizational solutions. However, just as well-being is more than just the absence of ill-being, physician flourishing requires more than just treatment of burnout. The HEAL (Hope, Engagement, Action, Lead) model, the subject matter of this paper, is a framework for instituting positive psychology practices to transform medical culture to address burnout and promote well-being for individuals and the healthcare system. This paper introduces the four pillars of HEALing, including specific interventions that may improve organizational cultures and aid in healing the system and the individual clinicians operating within it. Now more than ever in the era of COVID-19, solutions are needed to address this growing problem. Operating through the lens of positive psychology practices, informed by the unique culture of medical practice, healing our healers may be possible.