Dermatology within the United Kingdom is facing significant challenges on service provision. Dermatology registrars/trainees are the backbone for future National Health Service but there is a lack of literature on their career intentions following completion of training. We conducted semi-structured one-to-one interviews of ten senior dermatology registrars within the West Midlands. Information on demographics, career intention and factors influencing career decision were collected. A thematic analysis was used. The majority of trainees felt ready to become a consultant and considered taking up substantive consultant role. Personal and professional factors equally influenced career decision. Concerns related to training revealed three themes: individual support, organisational issues and training curriculum. The study highlighted trainees’ range of career trajectories is a multifactorial process. Our findings have provided an understanding of contemporary issues within dermatology training from a more personal level and the data may offer an important avenue for future research within dermatology education.