The unique experience of swimming the English Channel is a test of mind and body to overcome multiple challenges. The purpose of this study was to examine psychological characteristics and reflective meanings of these swimmers. Eight English Channel swimmers were interviewed. Inductive and deductive analyses compared interviews and interpretations with the coinvestigator and swimmers. Themes included the cognitive orientations of mental toughness, while cognitive strategies included goal setting, Compartmentalization of time, and/or swimming distance, and self-regulation. Descriptions of the experience of the swim included an ease of swimming at the beginning, more aversive experiences in the middle, and a paradoxical euphoria and letdown upon completion of the swim. Several swimmers noted the perception of increased occupational effectiveness, self-confidence, and an awareness of unlimited potential. Whereas, other swimmers noted a more competitive post event focus. Reflective experiences supported Maslow’s notion that the meaning associated with a peak experience augments daily life.