The purpose of this study was to examine how Olympians experience the transition to a second career, to identify the strategies they may or may not implement in order to prepare for it, and to determine the main factors that influence this process. Using a phenomenological approach we asked 26 Spanish Olympians (13 men and 13 women) from different summer Olympic sports about their experiences when it came to preparing for and entering a new place of work. The results revealed two main groups. The ‘strategists’ were Olympians with an awareness of their future and a deep understanding of their work environment, who took specific steps (academic training, entering a new job before ending their sporting career, saving money, taking advantage of their sporting capital and voluntary retirement) in order to enter their second career. The family was shown to be a key influence for Olympians in this group. At the other end of the spectrum were the ‘non-strategists’, those who did not combine their career in sport with an academic or vocational career. What set these Olympians apart was a lack of awareness regarding the need to prepare for their future career and that they did not implement strategies that might help them in this regard. In this group the family appeared somewhat indifferent to the question of what would happen when the athlete’s sporting career ended. These findings could serve as a platform from which to develop programs and assist athletes according to the group with which they are identified.