This article reports on the findings of a research project examining how to create a profession that is attractive and fulfilling for new and existing school leaders in two different municipalities in Sweden. The project set out to explore how work environments, career structures, salaries, and working conditions can contribute to attracting, retaining, and motivating school leaders to stay longer in the profession. To realise this objective, the study adopted a qualitative research design. Data was collected by carrying out semi-structured interviews with a sample of five school leaders in two different municipalities to investigate their experiences and views of the profession. The findings demonstrate that school leaders’ working conditions play a more critical role in their decisions to stay or leave the profession than financial compensation. The study also shows an unequal allocation of resources, both in terms of support functions and the limited time available for in-service education.