A stable teacher workforce is developed through a combination of quality preparation and tailored support. This study offers different lenses for the development of an in-depth understanding of professional experiences and the implications of professional experiences for initial teacher education (ITE) and early career teachers across international borders. In a globalized education environment, transnational research facilitates the acquisition of an in-depth understanding of the challenges encountered in ITE programs. These programs are frequently criticized for the quality of preparation of prospective teachers for teaching. Teacher preparedness, high expectations, targeted support, leadership awareness, and wellbeing lived experiences are concerns that if left unresolved over an extended period, will influence the confidence of preservice and beginning teachers, with implications for their career decisions. This qualitative study involved preservice and beginning teachers (n = 151) and their mentors (n = 123) from South Africa, as well as preservice and beginning teachers (n = 144) and school leaders (n = 763) from Australia. The research design was based on the context-conscious understanding development (C-CUD) theory, as a comprehensive theory to support the reflecting awareness of the context impact on preservice and beginning teachers. The findings unveil preservice and beginning teachers’ perceptions about lived experiences during professional learning and the perceived gap between theory and practice. In addition, the findings highlight expectations based on teacher standards and classroom challenges, as well as the realities teachers encounter even before entering the workforce and how these could be overcome.