Self-leadership is an enabling process during which a male student nurse learns to know himself better. This enriched self-awareness enables him to steer his work life. Male learners in the nursing profession could face gender-based challenges during their training that requires self-leadership. The study described the best experiences of self-leadership by male learner nurses during their four-year training programme at a nursing college in the Western Cape Province. A qualitative, exploratory, descriptive, and contextual design, incorporating the philosophy of the Appreciative Inquiry paradigm, was used. Purposive sampling was applied and 12 individual, semi-structured interviews were conducted. Data analysis indicated that peak experiences occur on multiple levels and include learning from ‘error’. Self-leadership could be enhanced by support from lecturers and mentors, fellow students, as well as by support in the wards and simulation laboratory.