This qualitative study furthers educational theory and research related to resilience and personal transformation. It develops connections between existing educational resilience research and change theories, and it utilizes these bodies of scholarship to propose a theory of personal transformation. Based on interviews with students who were successful in university after either not graduating from high school or graduating from non-academic high school programs, a metaphor of a Mobius strip is developed to hypothesize a theory of transformation as a means of understanding the students' journeys.