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Co-mentoring circles were developed, refined, and evaluated over the past seven years as safe, learning-filled spaces for aspiring educational leaders to come together to discuss their work as K-12 principal or program administrator interns and learn about leadership together. Co-mentoring circle formation elements include: using group agreements, holding confidentiality, deepening communication skills, giving and receiving feedback, reflective practice, developing trust, and taking part in ongoing assessment of the circle’s work. Three specific activities are used in the circle’s formation and are called: “hopes and concerns,” “the professional timeline,” and the “self-portrait.” We report the outcomes from the self-portrait (an auto-ethnography) activity and describe how this activity enhanced the development of the co-mentoring circle and circle members’ reported leadership lessons.