The individual differences literature has suggested that age, generation and career stage are related to a range of individual and organisational outcomes. In an employment context that is becoming increasingly characterised by instability, job insecurity, and responsibility for one’s career, individual perceptions of employability and job insecurity are important concepts to explore. However, age, career stage and generation differences in perceptions of employability and job insecurity have received modest attention. The main aim of this study was to explore the relationships between age, generational identity and career stage and the impact that these factors had on perceptions of employability and job insecurity. Aside from the main focus of the present research, this study also aimed to develop a measure of generational identity, as previous research relied on generational measures derived from age that limited the inferences that could be drawn from such research. However, this measure needed more development in order to be used in the main study. Five hundred and nine participants from a range of organisations participated in the main study, completing an online questionnaire containing measures of career stage, perceptions of employability and perceptions of job insecurity. As expected, measures of age generation and career stage were interrelated, providing support for the empirical literature and highlighting the importance of longitudinal research designs in age research. In line with the literature, low perceptions of employability were related to increased perceptions of job insecurity. In particular, Baby Boomers were found to have higher perceptions of job insecurity, as a result of lower perceptions of employability. Generations X and Y were found to have higher perceptions of job insecurity through higher levels of overall career concern. This paper provides support for the relationship between perceptions of employability and job insecurity in the changing employment context. It offers a platform for further empirical research regarding generation differences at work, and further exploration of the concepts of career stage and concern with ones career. Practical implications and directions for further research are discussed.