It was only after 1980's that great influx in to women entrepreneurship was witnessed. However, challenges faced by women entrepreneurs involves among, others, financial, human capital, network, cultural/normative challenges and government regulations. Yet nowadays women are more and more starting businesses and acting entrepreneurial for many reasons. These could be either of push (necessity) factors and/or pull (opportunity) factors. The paper examines challenges and motivations of 180 women entrepreneurs in Somali Region of Ethiopia who were purposively selected for the study. Administered face-to-face survey was conducted with 160 women entrepreneurs. The result of the paper shows that women entrepreneurs need demand creation in the area of microfinance loan applications. Women entrepreneurs start their businesses with their own personal savings and loans from family and friends, which is constraint to continuation of their businesses. Cultural challenges were not found to be barrier to women entrepreneurs in this paper, but the network challenges and government regulations were found to be challenges to women entrepreneurs. The paper also found that women entrepreneurs are motivated by the desire to generate income and become independent.