The regulation of occupations such as aviation pilots can result in their facing the shock of losing their medical certification and thus, their license to work. What are the issues that these former pilots face upon losing their medical certification? The key issues may take the form of protean career characteristics and mechanisms such as identity, adaptability, and agency, which may help the individuals match to a new occupational environment. The method of convergent interviewing is used to inductively acquire the key common issues that arise when pilots lose their medical certification in Australia. The results indicate that the clarity and strength of the pilots’ sense of occupational identity may amplify the impact of the shock when that career is denied to them. The findings highlight the importance of adaptability, although the reliance on adaptability varies depending on the pathway chosen to respond to the shock. Those in situations with less adaptability, agency, or support may be most in need of career and mental health counseling. Support and adaptability may be particularly important for those facing career shocks in occupations with substantial investments in their career identity.