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This phenomenological study describes the experiences of twelve leadership educators who were teaching leadership in undergraduate leadership development programs in the Midwest. The central research question was: What are the experiences of educators who are teaching leadership to undergraduate students at academic institutions? Teaching leadership was defined as providing developmental opportunities (e.g. formal education, in class instruction, one-on-one, coaching, service learning, individual reflection) to increase both leader and leadership capacity. Educators were defined as individuals who provide developmental opportunities for undergraduates. Participants had at least three years teaching leadership at the undergraduate level and were currently teaching a course with the explicit objective of increasing leadership capacity. Four themes emerged from the semi-structured interviews: (a) “I teach leadership. What does that mean?”, (b) “not dancing alone” in the learning community, (c) helping students make a difference, and (d) the educator’s journey: “a place of becoming.” The essence of teaching leadership was about parallel journeys: the students’ journey of leadership development and the journey of self-development of the educators.