Resident physicians are at higher risk for depression, anxiety, and burnout when compared with same-age peers, resulting in substantive personal and professional consequences. Training programs across the country have acknowledged the gravity of this situation and many have implemented programs and curricula that address wellness and resilience, yet the benefits of such initiatives are still largely unknown. While the development of wellness programming is well intentioned, it is often incongruent with the residency training environment. The mixed messaging that occurs when wellness programs are implemented in environments that do not support self-care may unintentionally cause resident distress. Indeed, outside of the time dedicated to wellness curricula, residents are often rewarded for self-sacrifice. In this commentary, we describe how the complexities of the medical system and culture contribute to mixed messaging and we explore the potential impact on residents. We offer recommendations to strengthen wellness programs through efforts to promote structural change in the training environment.