As stress impacts the organization and operations of a school, leader stressors may be determined by the setting, years of experience of the leader, and the greater educational landscape in which the principal must lead. The researchers sought to differentiate between the perceived stress and joy of urban and rural school principals. Findings derived from this time series design inquiry suggest that despite external influence, there is limited change in reported stress of rural school principals. Though the leadership in any setting is complex and multi-faceted, the researchers identified and assessed contributing factors.