This study examines the impact of a pedagogical strategy using individual life mapping as a foundational piece of a graduate educational leadership program. We argue that active learning opportunities, like life mapping, allow educational leadership students to explore more fully their sense-making processes about systems leadership, which is foundational to their developing mindsets and leadership skills. Jäppinen (2014) suggests that educational leadership programs should aim to allow students to make sense of the complexity around them and study the viewpoint of collaborative non-linear human interactions in their journey to leadership. Data and artifacts were collected from 41 graduate students; their ages ranged from 29 to 65 with the median age being 46. All the participants were enrolled in the closed-cohort, executive educational leadership program working toward an Educational Specialist degree and superintendent certification. The final condensing of the initial categories into macro-level themes illustrated that students perceived the life mapping activity as a catalyst for learning about themselves and others, building a successful cohort, and affirming their decisions to become systems leaders.