The period of student teaching often creates crisis experiences in student teachers and can have various negative effects, but it also offers opportunities for deep learning. This study focused on the types of struggles student teachers encounter and on the effects of coaching aimed at the promotion of core reflection. Core reflection is an approach focusing on the tension between people's inner strengths and their inner obstacles, as a way to support growth. While previous research suggested that teachers were able to improve their classroom performance due in part to core reflection's influence, no study before this one has directly explored how core reflection addressed uncertainty experienced by student teachers. Additionally, this study indicates core reflection may aid student teachers with finding a personal, authentic way of teaching -- a process one may call a Hero's Journey.