This paper examines why healthcare workers transition into underqualified employment and under what circumstances this occurs. There is a shortage of qualified healthcare professionals, so conventional measures, such as expanding training or improving working conditions, have not been effective. The requalification and validation of skills among experienced, underqualified care workers have not received much attention despite their potential. People with extensive experience but no formal qualifications are often overlooked, even though they could help reduce the skills shortage. In Germany, approximately 21% of employees are formally underqualified, and similar rates are observed in countries such as France, Finland, and the United Kingdom. This study employs Bourdieu’s social class theory and a sociology of knowledge approach, utilizing a documentary method that incorporates narrative interviews. The findings indicate that transitions into underqualified employment are frequently triggered by opportunities or chance events within the social environment. However, these are processed differently depending on individual circumstances and dispositions. This pattern is evident in transitions into nursing, education, and the broader labour market. The analysis reveals that institutional and social factors influence biographical transitions. While institutional transitions, like completing training, are clearly defined and formally recognised, social transitions, such as the end of parental leave or unemployment, tend to be less structured and more unclear.