This paper demonstrates the importance of studying insecurity in relation to identities at work. Drawing upon empirical research with business school academics in the context of the proliferation of managerialist controls of audit, accountability, monitoring and performativity, we illustrate how insecurities in the form of fragile and insecure academic selves are variously manifested. Emerging from our data were three forms of insecurity – imposters, aspirants and those preoccupied with existential concerns and we analyse these in the context of psychoanalytic, sociological and philosophical frameworks. In so doing, we make a three-fold contribution to the organization studies literature: first, we develop an understanding of identities whereby they are treated as a topic and not merely a resource for studying something else; second, we demonstrate how insecurity and identity are more nuanced and less monolithic concepts than has sometimes been deployed in the literature and third; we theorise the concepts of identity and insecurity as conditions and consequences of one another rather than monocausally related. Through this analysis of insecure identities, insightful understandings into the contemporary bittersweet experiences of working in academia, and specifically in business schools are developed that could prove fruitful for future research within and beyond this occupational group.