Many active ageing policies are inspired by the idea that sustainable careers may extend individuals’ working lives through their impact on career satisfaction and employability. However, empirical evidence on these assumptions remains scarce. Few studies on the transition to retirement take a career perspective. In this chapter, we investigate how career competencies influence the intention to retire through their impact on self-directedness, career satisfaction and employability. We thereby focus on two career competencies: self-awareness and adaptability. We examine how self-awareness and adaptability impact self-directedness and how employability in the internal and external labor market as well as subjective career satisfaction mediate the relationship between self-directedness and the retirement intention of older workers. Path analysis using a sample of 285 workers aged 50 or older reveals that self-awareness increases self-directedness, which, in turn, relates positively to external employability and career satisfaction. External employability and career satisfaction decrease the retirement intention. We did not find a mediating relationship via internal employability. The same counts for adaptability. In addition, adaptability is also related directly to retirement intention. We discuss the implications of these findings for research and practice.