This chapter is the product of a qualitative research based on 15 in-depth interviews with upper-level managers in Italy who lost their job when they were in their 50s. The research aims to contribute to an understanding of social processes that shape the lived experience of attempted transitions from unemployment among older workers. Drawing on the interview materials, it shows how age discrimination and common discourses about ageing and work in the contemporary Italian labour market limit the options available to older workers to successfully revive their career. Being discriminated against on account of age was described by interviewees as a frustrating experience that led them to construct a negative stereotyped character that they used to describe older workers and to distance themselves from this identity. Consistent with neoliberalism, work-related problems that may occur when one experiences late-career job loss were attributed by interviewees to an assumed decrease in the usefulness of workers as they age, and the responsibility for finding a solution to these problems was laid entirely on individuals’ shoulders.