Entrepreneurship is considered as one of the vital forces of economic development as the activity of entrepreneurs spurs change through innovation. Given that, it seems important to explore what factors and/or characteristics lead some individuals to choose the entrepreneurial path and take their entrepreneurial journey in a progressive direction. It is the researcher’s primary observations that people who come out as innovative entrepreneurs may not necessarily have drastically different circumstances or opportunities and resources as compared to their non-entrepreneur fellows. This hints that cognitive as well as physiological aspects of an individual may also contribute to their entrepreneurial temperament. Therefore, this study approaches entrepreneurial temperament from the psychological aspect. And, for the purpose of delimitation, special focus has been laid on the role of willpower or willingness in the lives of entrepreneurs which later led to pick the entrepreneurial path and stay steady. Therefore, the role of willpower has been investigated within the context of other psychological factors as well as in relation to the basic external factors. The qualitative case study approach is used in which multiple cases were formed for the comparative analysis to distinguish between entrepreneur and his/her classmates. In each case, an entrepreneur along with his/her 4-5 class fellows of last academic qualification (making an effort to control some of the factors like common resources and learning environment of some years) were interviewed through semi-structured interview guide following life course approach. Results show that despite not having any considerable social or financial advantage over their counterparts, the entrepreneurs made extraordinary career-moves and most of their significant activity had willpower or its corollaries such as greater internal locus of control, or higher self-efficacy, at its core. Some entrepreneurs even had lesser resources and opportunities as compared to their non-entrepreneur fellows but their willpower drove them ahead in the progressive stream of entrepreneurial dimension. Along with willpower, entrepreneurs are found less likely to engage in counterfactual thinking, showing confidence and less risk averse behavior in their professional (entrepreneurial) journey as compare to their peers. The study also includes some suggestions that may provide some important insights to the policymakers for providing a setup that can foster more successful entrepreneurs and promote this career-dimension among the potent individuals Supervisor:- Dr. Junaid Alam Memon