Career transitions are often studied from the perspective of changing from one career to the next. Missing from this definition, however, is that transitions can take place within a career. In the case of teacher education and academia, these transitions are often seen as well laid out with an accepted view of 'success' and those taking an alternate path being viewed as 'less successful'. In this self-study, three teacher educators at different stages of their careers were guided by the question: What are the barriers and enablers faced by teacher educators in relation to career transitions? The objective of this paper was to reconsider the notion of career transitions and trajectory. Situated within a small-scale research paradigm underpinned by interpretivism, this self-study presents an analysis of the 'stories' of three teacher educators and their lived experiences of career transitions within the academy. A descriptive case study approach was used to guide data collection over four phases to generate data using a narrative inquiry approach using timelines, individual portraits, collective stories and additional insights from a critical friend. The notion of critical friend was employed in two ways: the participants acted as critical friends for each other, and the fourth author challenged thinking and offered new perspectives. This self-study offers insights about the characteristics which have enabled and challenged the three teacher educators and may resonate with others, contributing to our understanding of conditions which can be created to support the intra-academy career transitions and professional development of teacher educators.