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This auto-ethnographical case study explored the ways the mentoring relationship between a late-career educational leadership professor and an early-career protégé influenced their well-being and enabled them to flourish personally and professionally. The study was guided by the following research question: In what ways, if any, does the mentoring relationship influence overall well-being? The findings indicated that both the mentor and the protégé perceived that their well-being had been positively influenced by the mentoring relationship in all five of Seligman’s (2011) PERMA domains often used to measure well-being. The study resulted in the creation of a model using mentoring and positive psychology concepts for high-quality and sustainable mentoring relationships.