The journey towards becoming a Clinical Psychologist is widely recognised as rigorous and challenging. This thesis aimed to explore the experiences of aspiring and trainee clinical psychologists in these early career stages. Part A of this portfolio presents an empirical paper focusing on aspiring psychologists’ experiences of the application process for the Doctorate in Clinical Psychology (DClinPsy). The aims of this study were to increase understanding of aspiring psychologists’ wellbeing when faced with the emotional challenges of the application process, and the journey of learning about themselves. The analysis suggested that for many aspiring psychologists, the application process impacted on their sense of self-worth, personal life and wellbeing. Connection and support from others appeared important in managing the emotional challenges during the process. Part B presents an empirical paper which explored trainee clinical psychologists’ experiences of the expectations and the reality of the doctorate, and the impact of expectation-reality mismatches on trainees’ wellbeing. The analysis highlighted the collective idealisation of the doctorate in the aspiring psychologist community, and the impact of holding idealised or more balanced expectations of the doctorate on trainees’ wellbeing. Discrepancies between expectations and reality related to a psychologically safe training environment impacted trainees’ wellbeing in both positive and negative ways.