The objective of our research is to analyse career dissatisfaction through the psychoanalytical lens of Jacques Lacan. Taking a multiple-case study approach, semi-structured interviews were conducted with seven male, senior managers working in the highly competitive technology industry. We found that respondents are defining satisfaction against a socially constructed career system that obliterates the concept of an agentic self. By grounding our qualitative investigation in the research fields of career and career dissatisfaction in the under-researched realm of Lacanian theory, we extend career theory to include a psychodynamic lens. We also contribute to practice by providing an alternative approach to career counselling that encourages the client to co-construct a sense of liberation and empowerment.