Teaching is a complex profession. Much of the work of teachers is hidden from view, happening behind the scenes. It is not until one becomes a teacher that they fully understand the complexities. Preparing teacher candidates before they enter their own classrooms for the potential tensions between their individual perspectives and educational contexts can support their development. This study explores the experiences of teacher candidates as they engage in reflection on and discussions about challenging scenarios they are likely to experience when they enter the profession. Through qualitative analysis of end-of-semester reflections, we identified salient themes including realization and assuredness related to the scenarios with which they were presented. Based on our findings, we share implications for teacher educators and school leaders to support novice teachers to recognize and take on the challenges they will undoubtedly experience. Creating productive spaces for teacher candidates to practice thoughtful adaptations may support novice teachers as they navigate tricky situations and may also impact teacher retention.