This study addresses some limitations related to knowledge of the circumstances that contribute to perceptions of downward or horizontal occupational mobility as a positive experience, increasing work satisfaction, labour market security, and maintaining subjective well-being. In pursuing this objective, seven working-life biographies are examined that demonstrate causes of occupational mobility, the investment needed for transition and stabilisation, as well as attitudes towards the destination occupation. Although a sense of meaningful work helps individuals accept a reduced income, interviewees treat it as a transitional period, seeing a possibility for at least some increase in salary. Maintaining one’s original social networks while accepting a less qualified occupation also contributes to preserving individual well-being. These aspects are more pronounced in women’s life stories. A more ambiguous attitude can be seen in the experience of men who encountered occupational and financial decline. While decision-making awareness, confidence in one’s choice, and control of the process helps to stabilize potential frustration caused by decline, some isolation from previous networks appears in the keeping of distance, reducing contact intensity, or staying abroad for longer periods. Perhaps to regain their subjective sense of well-being, the former implements the principle of ‘discrete stages’ in their social life, a notion that reflects the situation of their working life.