Although it might be considered the domain of many research areas, self-employment has not been studied vigorously. We draw upon the ideas of related areas to develop a sound design for the study of self-employment. Using retrospective career life-history data from West Germany, we model the process by which individuals move into and out of episodes of self-employment. Specifically, we examine: (1) the process of entry into self-employment at various stages of the career; and (2) the career differences between the self-employed and the conventionally employed. In general terms, the findings show that those factors which account for one stage of the self-employment experience do not necessarily account for others. More substantively, our findings point to the strong effects of social structural variables, especially those related to the family, as well as to the effects of previous self-employment experience.