The phenomena of an aging population, changing social and economic circumstances, as well as the existential necessity of mid-life changes form the background to this investigation. Though statistics indicate that there are only a few who have considered entrepreneurship as a desirable and feasible career option in mid life, the option is becoming more attractive as the possibility of lifetime employment with a single employer becomes increasingly remote. The focus of this article is to understand what has motivated first time entrepreneurs in midcareer to consider this choice and how they have made sense of their mid-life situations to successfully discover and exploit entrepreneurial opportunities. This study has demonstrated that it requires the optimal interaction of four key elements to increase the likelihood of a positive outcome of entrepreneurial pursuitsknowledge, networks, rewards and risks.