Background: A statewide 6-month school administrator health and wellness program encouraged participants to use a fitness tracker to self-monitor their physical activity and sleep patterns. The purpose of this study was to examine participants' experience in a school administrator health and wellness program and their perceptions of the impact on health-related behaviors, including activity/movement, nutrition, and sleep. Methods: Each of the 45 participants completed a semi-structured interview at three points in the program. Questions were designed to discern school administrators' perceptions of their ideal health and wellness balance at home and work. Results: School administrators reported new insights into their own well-being, benefits of social supports in their personal wellness journey, an expanded understanding of their ideal health and wellness balance at home and work, and a stronger sense of serving as a role model who needs to take care of him/herself. Conclusions: Although the program was helpful in establishing an ideal health and wellness balance at home and work for some school administrators, future programs should better emphasize nutrition and scaffold opportunities to maintain new habits following program completion.