The roles and aspirations of Assistant/Deputy Principals (AP/DPs) have received attention for a number of decades. In contrast to much of the reported research that either highlights the administrative and management tasks or foregrounds principal succession, we explore levels of satisfaction that play into DP/APs' interpretations of the realities of their professional experiences during everyday work. Job choice theory provided us with the theoretical resources for the exploration. Our study found that half of all participants perceived their job as a legitimate terminal career. They expressed immense satisfaction in the role, perceived the role as offering a sufficiently high level of challenge without the demands of ultimate leadership responsibility and identified interpersonal relationships, particularly those within the senior leadership team, as the most significant dimension in the role. However, the study has also highlighted that without the support of induction programmes, mentoring support and in-depth leadership training, for many AP/DPs 'on the job' training is the only means of learning available to support their professional development in the AP/DP role.