Using Australian labour force data, both cross-sectional and longitudinal, this study examines the dynamics of self-employment with a particular focus on workers transitioning between self-employment and salaried employment, and the extent to which self-employment is the result of workers’ observed and unobserved characteristics or is instead determined by their prior employment experience itself. Probability models of self-employment using both pooled-panel probit and dynamic random-effects panel probit methods are estimated, and the results are found to be extremely sensitive to the differences in the econometric methods. Once unobserved heterogeneity and initial conditions are controlled for in the dynamic model, the importance of observed characteristics in determining self-employment is greatly diminished. Instead, workers’ past experience in self-employment (as opposed to salaried employment) is found to have a large favourable effect on their future self-employment prospects. The influence of this state dependence is also considerably more important in determining self-employment outcomes than salaried ones. Despite establishing the importance of state dependence, however, what this effect implies about why individuals choose to become self-employed or the role that self-employment plays in the labour market remains unresolved.