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The purpose of this study was to examine the perspectives of retired principals who served as mentors of new school principals. The mentors described the contexts of current principals’ work and contrasted them with their own experiences of being principals “back in the day”. Mentor narratives of their own ‘days’ in addition to their year- long interactions with new principals revealed the changing demands and challenges faced by current principals. The results of the study emphasized the potential for mentoring in leadership development programs. A mentoring focus on principal personal socialization and identity development can allow principals to see themselves as social justice and equity advocates.