Burnout and depression are major problems facing physicians, with 300 to 400 physicians dying by suicide each year. In an effort to address this issue, the Accreditation Council for Graduate Medical Education (ACGME) revised the Common Program Requirements for residency and fellowship programs to include a strong emphasis on well-being, and this revision has been extended to including a subcompetency on well-being in the Milestones 2.0. The Psychiatry Milestones 2.0 Work Group was convened to draft updated psychiatry milestones. As part of the open feedback period, the American Association of Directors of Psychiatric Residency Training submitted an organizational letter outlining several points to consider regarding the original draft of the well-being subcompetency. The ACGME was receptive to this feedback and allowed the Psychiatry Milestones 2.0 Work Group to revise the subcompetency. Current research indicates that burnout is largely driven by systemic factors, but well-being literature and initiatives often focus on individual factors and responsibility for burnout rather than systemic change. Program directors tasked with assessing resident well-being can additionally encounter several professionalism concerns, including how to (1) define a subcompetency within a competency that itself has not been well defined; (2) decide the appropriate balance between individual and systemic responsibility for well-being; (3) consider mental health as a parameter of well-being; (4) balance roles as physicians, psychiatrists, and training directors in thinking about the mental health of residents without overstepping boundaries and while maintaining privacy, confidentiality, and resident safety; and (5) measure well-being in a sociocultural context. This article describes how these considerations were incorporated into the revision of the Psychiatry Milestones 2.0 version of the well-being subcompetency, which has subsequently been made available to other specialty work groups for potential use as they develop their specialty-specific Milestones 2.0.