One of the most typical features characterising modern ways of living and working is represented by the dynamism required by individuals in navigating their career paths. This article explores some case studies of career development collected through biographical interviews carried out within the Italian strand of the Cedefop project. These relate to individuals showing different levels of career dynamism (from very active micro-entrepreneurs up to subjects who had to give up their career-related aspirations because of disabilities). They demonstrate, powerfully, three main drivers of career development: reflexivity, self-identity and resilience. Some theoretical references regarding such drivers are here briefly taken into account through a specific conceptual framework. Where the case studies hint at these drivers, and allude to the role played by career guidance, extracts are presented verbatim. In the concluding section, the need for new further research in this field is emphasised, both at the theoretical and at the empirical level.