Existing literature on entrepreneurship often regards job dissatisfaction as an entrepreneurial push factor and self-efficacy as an entrepreneurial pull factor. The argument is that individuals who are dissatisfied with their jobs are more likely to seek alternative mode of employment such as self-employment. On the other hand, personal abilities such as self-efficacy may pull individuals toward starting their own businesses in areas where they are confident and competent in. Despite the importance of job dissatisfaction and self-efficacy for new venture creation, few if any studies have examined the entrepreneurial phenomena from a holistic perspective. Utilizing concepts from the P-E fit and self-efficacy literatures, we specifically examined how IT professional’s personal attributes such as innovation orientation and self-efficacy condition individuals for an entrepreneurial career in unsatisfactory work environments.