This chapter explores the role of individualization in careers, and especially with regard to older workers. The central aim of the chapter is to elucidate the role of individualization in the establishment of careers, as well as how organizations treat their workers, and employ HRM systems and practices in order to retain and motivate workers of all ages. Based on the argument that the older workers become, the more heterogeneous they become in terms of career preferences, I propose that individualization of career arrangements will be increasingly important in the sustainability of contemporary careers. An individualized approach, such as through the lens of idiosyncratic deals (or I-deals), can facilitate older workers to retain work motivation and performance. However, the extent to which I-deals will benefit motivation and performance is dependent upon a range of factors, including supportive climate, psychological processes that occur within the worker, and fairness in the distribution of negotiated deals across the organization.