This capstone recounts a story of two merging paths. The first path is a story of navigating a life-changing medical diagnosis, self-realization, and managing transitions. The second path is a story of personal development via experiences and key learnings from the University of Pennsylvania Master of Science Organizational Dynamics program. The two paths are purposefully intertwined in a story format to reveal the zigs and zags of personal growth, as well as the literature and teachings that shaped me while navigating a new normal. This capstone focuses on topics of introspection, managing transitions, dealing with ambiguity, and organizational leadership. I hope this paper serves as an inspiration for those undergoing a personal transformation or navigating ambiguity as the result of a life-changing event. The paper shows how organizational change and leadership frameworks have tremendous value when used as reflection tools at an individual level.