This article aims to contribute to the debate of how theoretical concepts can be operationalised when researching educational issues. Specifically, it examines the application of the concepts of social and cultural capital in empirical research seeking to provide explanations for educational processes relating to post-secondary school choice making in contemporary Cyprus. The article argues that there are limitations in the various ways social and cultural capital are operationalised quantitatively in empirical research as often they do not capture adequately the full extent of the social dynamics that they draw attention to. Instead the use of qualitative methods where the researcher probes for details into the practices, habits, beliefs, and attitudes of individuals are seen as having powerful exploratory and explanatory potentials to address these limitations. (Contains 6 tables and 2 figures.)