This paper presents the results of an exploratory research project about the perception of aspiring principals regarding the challenges of beginning principals and the support that they need. These aspiring principals are participants on the Leaders in Education Programme (LEP) in Singapore. According to the research findings, the LEP participants perceived that the main challenges they were likely to face if and when appointed as principals would be adapting to a new environment and role; working with staff and other stakeholders; and meeting the expectations of others while trying to live true to one's values. The support they felt they would need as beginning principals was a network of professional peers; guidance from an experienced mentor; and access to the expertise of academics and continuous professional development platforms. Interestingly, while Singapore appears to have a reputation for a focus on examination results and quality assurance measures, the participants hardly mentioned any challenges or need for support in these areas. The paper calls for a greater level of understanding and support for beginning principals in doing an increasingly demanding job in a highly complex environment.