Career development for university research managers and administrators (RMAs) is inherently challenging in small island states. In this article, we argue that by acquiring career adaptability resources, university RMAs can address their career development needs even in contexts with a restricted labor market. We do this by first identifying the factors that shape the career development prospects of university RMAs. Subsequently, we present evidence of how university RMAs in small island states may pursue their career development goals by redefining their roles according to the contextual realities. Career adaptability theory helps us to explore how this redefinition occurs, particularly since adaptability arises from a combination of personality traits (self-regulation) and careful interventions that can build adaptability resources. We use the knowledge from career adaptability theory to identify a number of implications for RMAs, universities, counselors, and professional associations to address career development issues within restricted small island contexts.