We examined supply-side determinants of transition from the wage and salary sector to self-employment of women and men living Poland. The empirical analysis was made possible due to a unique and under explored longitudinal survey—Social Diagnosis—that contains rare indicators such as job preferences and work events. The empirical results in the 2007–2015 period indicated that women and men transitioning into self-employment were differently motivated. In terms of job attributes, women found independence at work and for those in professional occupations a job matching their competences as a desirable job attribute, while for men the lack of stress, a good salary and independence was key. The analysis of work events and its influence on self-employment weakly confirmed the glass-ceiling hypothesis. In line with other research, our analysis indicated that financial constraints strongly determined the entry into self-employment. A key human capital determinant was past entrepreneurial experience indicating a slow, cautious transition process into self-employment.