The purpose of this paper is to explore tertiary student development in Trinidad and Tobago (T&T), with an emphasis on the intersections of two dimensions likely to be particularly relevant in a collectivist context like that of T&T: interpersonal and intrapersonal development. A multiple case study approach was used to emphasize the complexity of each participant's experiences and development while also allowing for comparisons to be made across cases. Findings reflect a close connection between interpersonal and intrapersonal development, reflecting aspects of both individuation/independence and connection/interdependence. The findings from this study highlight the practical utility of critical and collectivist perspectives on self-authorship development for student services professionals in T&T but also points to the ways in which student development theories can be adapted to better understand students in T&T and potentially other collectivist contexts.