This dissertation explores how economic, organizational, and personal factors affect self-employment transitions, occupational decisions, and firm formation activities of individuals at different positions in the skill distribution. The first essay of my dissertation studies how local unemployment rates differentially affect entry into self-employment by individuals at different places in the skill distribution. The empirical results show a positive correlation between local unemployment rates and entry into self-employment for low-ability workers, but not for high-ability workers. Including employer size to eliminate possible distortions showed that the positive association between unemployment and self-employment among low-ability workers is in fact driven by the small firm effect. Controlling for firm size yields a negative association between unemployment and self-employment among high-ability workers. Effects of organizational capital, human capital and physical capital, on the firm formation activities of people at distinct skill levels depend on the type of the industry which is chosen for the new firm. Two types of industries, capital-intensive and ability-intensive, are utilized to explore this hypothesis in the second essay. A capital-intensive industry requires more physical investment, and consequently more funds, whereas, an ability-intensive industry requires more human capital. It is shown that high human capital requirements are associated with higher earnings among the most able individuals, and therefore makes them more likely to found firms in an ability-intensive industry. Wealthy people are more likely to establish both capital-intensive and ability-intensive firms, even though the amount of funds necessary for two industry types differs. Moreover, entry into both industries is predicted to happen later in life due to the removal of entry barriers constituted by required investment spending using savings when old. Empirical mixed results are observed. The third essay investigates earning differentials between future entrepreneurs and their non-entrepreneurial colleagues. Results show that high-ability firm-owners in an ability-intensive industry were earning more than those that remained in wage-work, whereas, low-ability firm-owners in a capital-intensive industry were earning less than those remaining in paid-work.