The main objective was to further unravel the experience of motivation in an expert male skydiver by investigating: (1) his general experience of motivation and perception of the dangers of skydiving; (2) his pursuit of new challenges and learning new skills as factors in maintaining motivation; (3) evidence of a mastery-based confidence frame in his motivational experience. This was a unique case study informed by reversal theory. The participant’s perception of skydiving was that it was not a risky or dangerous activity and a primary motive for his involvement in skydiving was personal goal achievement. Maintaining control and mastery during skydiving was a key motivational element during his long career and pursuing new challenges and learning new skills was found to be important for his continued participation. Data indicated that his confidence frame was based on a telic-mastery state combination, which challenged previous reversal theory research findings and constructs.