Empirical studies indicate family concerns as a primary reasons why promising principals and central office administrators do not aspire to the superintendency (O'Connell, Brown, Guptil, Stosberg, & O'Connell, 2001; Volp & Rogers, 2004). Hesitancy to apply for superintendent positions is further complicated by the fact that the superintendency has largely been constructed in male images or archetypes (Jung, 1964), which are affected by context. And while psychology and sociology offer theoretically grounded empirical literature on work-family balance (e.g., Greenhaus & Beutell, 1985) and conflict (e.g., Sieber 1974), superintendents are not part of the sample. In-depth case study research was used to collect and analyze data on two effective rural superintendents (one female and one male) whose life conditions match three of the hesitancy factors (Rogers, Terranova, & Volp, 2006) associated with the next generation of school superintendents: having school-age children, spousal considerations, enjoyment (quality of life) factors. Participants were selected via snowball sampling techniques (Lincoln & Guba, 1993), and data sources primarily included narrative interviews with the superintendents and their family members (a total of 42 interviews). Documents such as the superintendent's calendar were also analyzed. Data were coded inductively and deductively into themes and subthemes (Glaser & Strauss, 1967). Two conceptualizations of balance emerge from the data: an integrated view (superintendency as lifestyle) and a compartmentalized view (equal time devoted to each life role). Furthermore, traditional perceptions of gender permeated findings related to life quality and superintendent effectiveness. Findings indicate that the "superintendency as lifestyle" perspective appears to be more compatible with the next generation of school leadership. The article concludes with implications for rural superintendent research, preparation, and practice.