While the role of leadership in improving schools is attracting more worldwide attention, there is a need for more research investigating leaders' experiences in different national contexts. Using focus-group and semi-structured interview data, this paper explores the background, identities and experiences of a small group of Jamaican school leaders who were involved in a leadership development programme. By drawing on the concepts of culture, socialisation and identity, the paper examines how the participants' journeys of becoming and being school leaders are influenced by national-level societal and cultural issues, experienced at a local level. The findings suggest that in becoming school leaders, the participants perceived that they had a strong sense of agency in attempting to change the social structures within the institutions they lead and in the surrounding local communities, which in turn, they hope, will have a lasting effect on the nation as a whole.