The purpose of this study was to describe the experiences of music educators at varying career stages and teaching positions who experience chronic illnesses. Participants (n = 8) represented a variety of chronic illnesses and self-identified career stages. Research questions centered on how participants described navigating their chronic illnesses and how their illnesses impacted or influenced their work. Data included individual and focus group interviews. We found two themes. The first theme connected to realities and misconceptions of illness, including living with ever-present and often invisible symptoms and unpredictable flare-ups, which led to silence and isolation. The second theme described how participants adjusted their work with an emphasis on flexibility, including personal and professional modifications and considerations due to COVID-19. Recommendations are described in terms of professional support, representation, understanding, communication, community, self-advocacy, and broadening the scope of teacher wellness.