This article is a collage of ideas and thoughts born out of a contrapuntal reading of the effects of colonial imagination and postcolonial conditions on educational practice in the Caribbean. It is an article which sustains a pedagogy of hope and which uses the epistemological space of academic writing for conceptualizing postcoloniality as an aspirational project. In the article are presented several narratives which are interwoven into conversations between historical and contemporary cases of critical pedagogy. Three themes emerge. Firstly, diasporic considerations are considered in relation to identity, where issues of translation and Creoleness are discussed. Secondly, educational practice and the Caribbean problematic make the link with the third theme, in which a historical case of professional practice is highlighted. The fourth theme proposes a practice of critical professionalism and juxtaposes that practice with the disposition of the subaltern professional. The article concludes with a claim that critical educational practice is a postcolonial aspiration which must be sustained on the hopefulness of the imagination of the Caribbean Diaspora. (Contains 1 note.)