The purpose of this paper is to explore some experiences of early Caribbean migrants, while offering comparisons between two similar school systems, namely England and Jamaica. The paper employs the autoethnographical method (auto/ethno/graphy), which is a study of self in context. Using the tool of memory, the autobiographical investigation of one set of migrant experiences confirms the commonality of educational systems and underscores the efficiency of colonial administration in managing the same lack of opportunities in two settings. The individual account of schooling in England revealed the impact and influence of family and the beginning of the racist practices that eventually became entrenched. However, the account also revealed the unplanned and casual opportunities that did arise for a child to navigate her way through the system. As the discriminatory practices hardened with time and legislation, there was increased alienation and the search by younger migrants for a better way of belonging through 'home' and community. The paper obliquely searches for the common grounds and routes shared by later migrants and descendants of migrants. The final aim of the paper has been to remind teachers of the wider possibilities for narratives in classroom encounters.