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Research regarding stress and burnout suggests the pressures of life as a principal are becoming more intense each year. Principal turnover is at 18-20% per year. The present qualitative case study used Seligman’s PERMA framework to explore principal personal and professional well-being practices to bolster longevity in the position. The use of informal mentoring over a twelve-week period resulted in enhanced knowledge and awareness of personal and professional well-being practices. Principals understood the relationship of flourishing leaders and faculty to a flourishing organization including the students served. One hundred percent (100%) of the participants reported that mentors are critical to increasing their understanding of well-being and how to connect this important knowledge to their personal and professional lives.