There is a debate in the entrepreneurship literature whether personality plays a role for the decision to be an entrepreneur. While empirical evidence often reveals a significant relationship between personality traits and the self-employment status, critics of the personality approach claim that differences among entrepreneurs might even be larger than differences among entrepreneurs and non-entrepreneurs. This paper draws on Holland’s (1985) theory of vocational behavior which emphasizes a key role of personality for individuals’ vocational choices. I examine empirically whether pro-entrepreneurial types of individuals are likely to make different vocational choices than those who prefer to stay in paid employment. Moreover, I investigate how personality affects entrepreneurial choice within occupations.