Transformative learning, introduced in 1978 by Jack Mezirow, describes the process in which an individual’s thoughts, feelings, and opinions on any given idea are changed from one perspective to another. Mezirow’s theory encapsulates the various, and often emotional, journey one experiences throughout their transformation requiring internal and external influences throughout four main theoretical components: experience, critical reflection, reflective discourse, and taking action. This capstone describes a deeply personal account of my transformative learning experience provoked by a disorienting dilemma, contrasted to the eleven phases of Mezirow’s Transformative Learning Theory. Additionally, my participation within the University of Pennsylvania’s Executive Coaching and Organizational Consulting Cohort is explored to feature the various ways the cohort fundamentally contributed to my transformative learning experience. This capstone aims to provide the reader with insight into the gravity of influencers on, and appreciation for the emotional impact of, an individual’s transformative learning experience.