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Research regarding stress and burnout suggests that the pressures of the principalship are becoming more intense each year, and school principals are leaving their jobs. The purpose of this phenomenological study was to explore mentoring as a way to combat the stressors of the principalship and focused on mentoring principals for well-being using Seligman’s (2011) positive psychology framework, PERMA. It explored principal well-being as reflected in mentoring practices. Nine school principals from different communities in Alabama were interviewed. Twelve themes emerged, and aligned with the five PERMA domains: positive emotion, engagement, relationships, meaning, and accomplishment. The findings revealed that the principals’ perceived that their mentors improved their confidence and overall wellbeing and decreased their stress.