Teacher educators pursue overseas higher education qualifications for better career opportunities in their respective institutions. However, the initiatives are not always met with the habitus and doxa to complete the desired degree as failures might impact their career development and lead to potential identity changes. This study attempts to reveal the stories behind overseas education failures shared by higher education teaching staff. A narrative approach was employed to explore further social, academic, and professional impacts experienced by the staff. Eight participants were purposively recruited to gain maximum variation and data richness. They were requested to complete written narrative frames to illustrate their stories. Data from this instrument were used to construct semistructured interview questions in the subsequent phase. Relevant academic and corresponding documents were also examined for corroboration. The results demonstrate that preparations in terms of academic, socio-cultural, and financial arrangements are crucial to those who aspire to pursue doctoral degrees overseas. Adaptation to academic and cultural life and relations with supervisors might contribute to the successful progression of the study. Further, family and social support from the surrounding environments are also essential in restoring their self-confidence. This study contributes to a novel insight into the essence of academic and non-academic preparations for those intending to pursue overseas doctoral studies.