For forensic psychiatry to thrive as a profession, practitioners need to be committed to intentional, continuous learning and development throughout their careers. However, carving their way through the challenges of practice and finding room to grow can be daunting. Research can help lessen this burden by examining the careers of experienced and skilled practitioners, identifying the factors that influenced their development, and the strategies they used to direct it. To date, little research of this kind has been conducted in forensic psychiatry. In this study, we used the deliberate practice model of elite performance as a heuristic to interpret the accounts of several experienced and distinguished practitioners, revealing and characterizing the influences and activities they identify as having been most important to their development. Semi-structured telephone interviews were conducted with six participants from across North America who started their forensic careers between 1965 and 1980. Transcripts were analyzed using directed content analysis. Participants cited little in the way of highly structured activities designed specifically to improve performance. They instead described using opportunities to learn from real casework and additional knowledge pursuits, as well as using deliberate career management to structure the conditions of their work-based learning. They also stressed the effect of entering forensic practice during a period of increasing interest, demand and investment, which yielded early opportunities to learn through practice. We discuss limitations in the deliberate practice model’s capacity to capture key learning strategies in forensic psychiatry, connections between work-based learning and the discipline’s general historical trajectory, and the role of career management in professional development strategies.