This paper explores the lived experience of leadership learning and development in a single case study of an entrepreneur participating in a major leadership development programme for owner-managers of small and medium-sized enterprises (SMEs). Based on autobiographical research, it provides a rich contextual account of the nature and underlying influences of leadership learning throughout the life-course and as a consequence of participation in the programme. Whilst the paper should interest scholars, policy makers and those concerned with programme development, it may also resonate with entrepreneurs and help them make sense of their experience of leadership development. (Contains 4 figures, 1 table and 1 note.)