Social and economic conditions, as well as the dynamism of the Chilean labour market, place new demands on middle-aged workers who have to explore both internal and external opportunities to develop successful careers. We assumed that possible self and identity in future states are core organizing aspects in this process. Identities, being core components of the self-concept, comprise self-representations that are contextually based and rooted in a social structure. Given the fact that there is a serious lack of empirical research in this domain, this study was aimed to help close an important gap in the literature. More specifically, it was intended to better understand the role played by possible selves and identity – that is, knowledge about what the self might eventually achieve or become – in career development. Based on an in-depth qualitative study among 25 male middle-aged Chilean managers, we found that the possible selves reported: (1) are evolving processes that vary in terms of content, stability and elaboration; (2) are related to career variety; (3) help in both career transitions and the adjustment process in novel situations; and (4) act as an incentive in career development. It is important to stress that in cases of challenging work contexts, employees are urged to create and recreate new selves and identities at work in order to increase their adaptability to ever-increasing working life demands and enhance their employability.