The aim of this study is to gain a thorough understanding for the reasons why and how some mid-career managers are able to leave corporate organisations to start their own companies in SA and what perceived factors make them successful. SA needs to develop entrepreneurs so as to achieve a 6% growth rate, in order to overcome unemployment and poverty. Twelve semi-structured interviews were conducted with successful entrepreneurs, who had already made the transition from corporate manager to entrepreneur. The feedback was analysed using a combination of narrative, content and constant comparative analysis. Convenience and snowball sampling generated a participant base that had extensive corporate experience, were well educated, had each been in entrepreneurship for many years and employed more than 1240 employees. The key findings were: (1) changing career – career reasons directly affect whether a mid-career entrepreneur (“MCE”) will engage in an entrepreneurial activity, as this is the basis of entrepreneurial intention, (2) motivation – human motivations directly influence who pursues entrepreneurial opportunities, and who persists and survives when challenges arise, (3) career development – both human capital and social capital are essential for success, and (4) entrepreneurialism – mid-career entrepreneurs gain considerable experience while in corporate which assist them to be a successful entrepreneurs. Years of corporate experience are the foundation for a MCE, as it provides knowledge, experience, networks and confidence.