Previous research on stress in the workplace has demonstrated that it can have not only a current, but lasting effect on a worker's health. The superintendency is a stressful job due to all of the competing demands of running a school system, no matter the size. This exploratory study reexamined qualitative interview transcripts from Robinson's (2013) study of female superintendents who left the superintendency, to look more closely at what stressors the superintendents' discussed and the relation of these stressors to their health. The women in this study found long days, outsider status, position requirements, visibility, relations with school board, and helplessness to be their greatest stressors. The effect of the stress caused issues with sleeping, eating, maintaining exercise, minimizing time off, and damaging relationships and friendships, unless women spent the time reclaiming their selves. Finally, the health results described included mental health issues, immune related diseases, chronic conditions, as well as life threatening illnesses. Recommendations for future studies include exploring the topic of superintendent stress, health and well-being on a larger scale. Were the findings of these selected female superintendents in Virginia comparable to women superintendents throughout the country? Are the stressors and their effects on health a phenomenon that affects women only, or do male superintendents experience the same problems and to the same degree as their female counterparts? A large-scale quantitative national survey of superintendent stress, health, and well-being would help explore this area from a different perspective.