Research continually shows that early career teachers struggle as they make the transition to the profession (Ewing 2006; Lortie 2002). Policy initiatives have been introduced in an attempt to ‘fix’ the problem and alleviate the struggles (Sullivan & Morrison, 2014). However, such initiatives have not always been successful because they tend to adopt a deficit view of teachers and ignore the interwoven influences of the personal, contextual and systemic issues that affect their work. This paper reports on a socially-critical study that examined 42 early career teachers’ trajectories and resilience. I created a data set from a larger study drawing on the traditions of narrative enquiry and critical ethnography which investigated early career teacher resilience (Johnson, et al. 2016). The data included line drawings and transcripts of semi-structured interviews that the team held with the teachers. The participants were asked to prepare and discuss a ‘line drawing’ to highlight the trajectory and critical points of their careers. The purpose of plotting their peaks and troughs was to guide them to reflect on their experiences to identify important events and contextual factors. This elicitation tool was adopted from Orland (2000) and Sumison (2004) to provide a visual tool for recording personal turning points (Tripp 1998) that highlighted issues of resilience. I analysed these data to make sense of the teachers’ critical turning points. This paper argues that systemic policies related to recruitment and retention, and the intense and isolated nature of early career teacher’ work contribute to not only their emotional despair but also to their elation. It argues that the central determinants of early career wellbeing focus on the specific strengths and weaknesses of individual teachers. By individualising these explanations, we tend to lose sight of bigger issues that impact on their wellbeing. That is, to understand the individual requires us to understand the institution (Mills 1970). Therefore, while there is some merit in mapping the ‘trajectories of despair and elation’ in early career teachers’ lives, we should avoid seeing these emotional highs and lows in individualistic ways. As Mills reminds us, we need to see the link between what may be happening in the lives of individual teachers, and the big events, movements and actions that are happening in the broader society. Finally, this paper contributes to the call to rethink the nature of early career teachers’ work to provide a better transition to the profession.