Researchers have written extensively about the transitional experiences of former athletes and theorised about how to affect healthy and positive outcomes for athletes. While some studies have revealed significant psychological distress amongst retired athletes, others have found no indication of adjustment difficulty. Thus, the present study took a more specific approach, and aimed to identify the factors which either influenced post adjustment difficulty or led to flourishing in transitioned athletes. Data was collected from 81 former elite New Zealand athletes by means of a questionnaire, distributed amongst various sporting codes and organisations. The questionnaire included measures of athletic identity, flourishing and emotional responses. Results indicated that athletes who had stronger athletic identities also had higher levels of flourishing after retirement. Furthermore, those who retired voluntarily demonstrated high levels of flourishing and less post sport adjustment difficulty in comparison to those who retired involuntarily. Planning for retirement also resulted in significantly less post-retirement adjustment difficulty. Additionally, female athletes who displayed high levels of athletic identity also experienced more negative emotions when dealing with retirement. These findings demonstrate the importance of planning and preparing for retirement, as it has the potential to lead to more positive long terms outcomes for athletes. A better understanding of athletic identity and the experiences of athletes who retire involuntarily will allow governing sporting bodies and sport psychologists the opportunity to identify early the athletes who may be more prone to adjustment difficulties, and intervene appropriately. The development and implementation of a proper athlete transition programme or process within New Zealand would better support healthy and smooth transitions out of sport, and lead to more positive outcomes for athletes.