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In this chapter, we explore the impact of a mentoring program designed to cultivate servant leadership(SL) virtues such as humility, courage, forgiveness, and empowerment on the wellbeing of K-12 school leaders. Despite the program’s primary focus on mentees, this study delves into the experiences of mentors—active and retired K-12 school principals—as they navigate the dynamics of mentoring relationships. Utilizing the PERMA wellbeing framework, we analyze data from mentors’ focus group interviews, revealing the profound impact of mentoring on mentors’ sense of fulfillment and joy. Our findings underscore the reciprocal benefits mentors reap, highlighting the interconnection between mentorship and personal growth. As educational leadership faces unprecedented challenges, our research reaffirms the enduring relevance of mentoring and servant leadership in nurturing the holistic wellbeing of school leaders and their communities.

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