The aim of this paper is to explore some crucial factors playing a significant role in employment decision-making. In particular, we aim at investigating the influence of family background on the choice to become a self-employed rather than a salaried; for this end, a series of regression models for categorical data are estimated both on sampled workers, taken as a whole, and by gender separation. In this light, to test if the occupational choice is context-dependent, environmental attributes are also modelled. In addition to a diversity of determinants, obtained results shed light on some differences between self-employed workers by first and second generation. Finally, by testing a two-level small area model, integrating the use of unit and area level covariates, we look into potential differentials of employment patterns across Italian regions.