This qualitative study aims to explore the valuable functionings—things that people consider to be important—of the older long-term unemployed and their ability to achieve valued outcomes. Semi-structured interviews were conducted with 20 long-term unemployed people aged 45 and over. Participants were included through purposeful sampling. The theoretical frameworks of the latent deprivation theory and the capability approach were used to develop an interpretive analysis. Nine valuable functionings were identified: social contact, feeling appreciated, structure, feeling useful, meaningfulness, autonomy, financial resources, paid work, and being active. These valuable functionings were partly accessible through the activities that people performed, varying from physically active and physically passive activities to informal work. The functionings of meaningfulness, autonomy, financial resources, and paid work seemed to be difficult to achieve. We identified three groups. The first consisted of people whose work status changed when they entered the benefit system; for them paid work was still a valuable functioning, and they experienced the most difficulties in achieving valued outcomes. The second group also experienced a change in work status once they started to receive benefits, but those people adapted to their new situation by attributing greater value to other functionings. The third group had no change in work status, e.g., housewives who had applied for a benefit because they were not able to make ends meet after a divorce. This group did not experience a loss of functionings due to unemployment, nor did they try to achieve other functionings. The results of this study indicate a need for a more personalized, tailor-made approach, with an emphasis on an individual’s valued outcomes instead of on rules and obligations.