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The arrival of retirement, whether it was keenly desired or feared, in the current social and political context, confronts the subject with a profound overhaul of his or her identity. Needing to find a new meaning for life, he or she is invited to redefine his or her relationship to space, time, him or herself, others, and the world. How does one live without working? By following the odyssey of Ulysses, a hero of the human adventure, we can approach the delicate questions that arise from retirement to life’s end. How do you separate from the career that has nourished you throughout adulthood? How do you give up your profession? How do you avoid being overwhelmed by temptations to isolate or even destroy yourself? With youth quickly disappearing, we are confronted by our own mortality. We must resist escaping into the past and the loss of meaning. Ordeals await us, but with a good guide, it is possible to navigate this passage, avoiding the obstacles. Each trial can teach us a new form of inner wisdom.