The objective of this study was to explore the business-career transition of people with disabilities. Through multiple case studies in Ecuador, the present study highlights the career obstacles to the venture of being a businessman. Those obstacles are derived from the impediments caused by poverty and disability. The effective management of this type of transition seems to come from a sense of strengthened coherence, self-esteem, vision, determination, and experience that the individual has. Those, together with environmental factors such as family and governmental support, propel entrepreneurship. The reasons for undertaking are out of necessity, desire, or use of opportunities, which allow the person to establish a new career, enabling social integration and well-being.