Cape Verde’s history of colonial neglect, drought, famine, and forced migration—coupled with its arid climate, poor resource base, and dependence upon foreign aid—has turned migration into a structural survival strategy. Cape Verdean identity is thus marked by a collective looking forward toward other geographical locations where relatives and friends have made a new home, and a collective looking backward—to relatives and friends left behind in what becomes an imaginary and desired homeland. Wherever Cape Verdeans are located, their identity claims are conditioned by this double-sided gaze: looking outwards toward the influences of other locations and of the external categorizations Cape Verdeans are subjected to by others, and looking inwards toward a more intimate “homing” space of memory, meaning, and self-ascription. The article explores these processes through a discussion of the challenges posed to young Cape Verdeans pursuing education in northern Portugal and examines how identity claims are constructed through nation, citizenship, and personhood, elucidating the ways in which these may become intertwined in processes of diasporization and of creolization. Cape Verde offers a paradigmatic case for distinguishing between creolization and creoleness since an analytical usage of the concept “creole” may be used to deconstruct normative interpretations of the term creole in social and political practice.