What does it mean for a person to move from work to retirement? What characterizes this experience? The significant demographic, economic and socio-cultural changes that have taken place recently have also had an impact on ways of achieving full withdrawal from work. Retirement is a difficult transition in which people lose some material and psychosocial resources, but they can experience new opportunities for enrichment and define new projects. However, this potential positive outcome is not promptly achievable and requires personal commitment as well as social and organizational facilities to master it. Retirement is not an event, but a process that begins to foresee progressive forms of exit and re-entry into a social reality to be defined by the person. Therefore, we do not refer to a simple or automatic conclusion of "active life", but to the possible construction of a new composite system of self-manageable activities that has to be supported by organizations and institutions. In the cultural imaginary, in fact, the condition of the elderly is associated with the idea of a general process of decay, deriving from a progressive loss of psychophysical, social and productive functions. The traits that are most frequently attributed to older people are those of weakness and disengagement, starting from the fact that the birth of the separation of old age from adulthood is anchored to the escape of the subject from the productive system. The lengthening of a lifespan is reshaping the structure and demographic profile of our society and the generational system, with consequences on the economic and social system. It represents one of the great challenges with important consequences for contemporary societies.