This article draws on the author’s personal experiences of engaging in ethically driven research and development in the Caribbean and Central America. Specifically, it explores how issues of transnational identity and belonging are constantly being renegotiated within the colonial matrix, and the position the author was accorded by the actors involved. These complex and nuanced processes led the author to reposition herself in relation to the various discourses shaping the encounters, with positive and negative results. It provides insights on how coloniality of power shapes such processes, creating conditions that bring about tensions and struggles.