Entrepreneurship is a stressful role for any person. Every enterpriser gets a pailful of stress, but how they handle it differ. To be in charge of leading people, making decisions, and determining the fate of your venture with your actions is not easy. The purpose of this paper is to fill this void by examining the depth and range of psychological stressors and strains that entrepreneurs encounter in their new venture creation. To further, clarify the confusion and inconsistencies in being self-employed. A three-stage research programme was devised. 24 South African-based entrepreneurs were interviewed and a total of 192 questionnaires administered to conference attendees. The study suggests that entrepreneurship is richly satisfying on one hand, but severely stressful on the other. Income usually doesn't buy happiness. Hence, by raising awareness, small business owners can come to terms with stress, thereby enhancing their careers, and lengthening their lives. The chapter concludes perhaps that stress is the psychological price of entrepreneurship.