In this study, the authors explored the journey of five secondary teachers for two years through their teacher education program and their first year of teaching. The findings revealed: (1) major concerns of the preservice teachers; and (2) teacher educators used strategies to help the preservice teachers face their concerns. During their student teaching experiences, participants were concerned about classroom management, keeping students motivated in learning the content, and parent involvement through knowledge of their children’s academic progress or non-progress as well as of their behavioral issues. The authors also noted that the participants expressed concern for making connections with diverse student populations. As first-year teachers, they fully understood their multiple roles as teachers and perceived teaching as more than content delivery.