The study aims to explore the barriers towards the enterprising of cooperatives in Sesheke District of Western Province in Zambia. This is against the background that cooperatives have not been enterprising for over a decade. Thus, the research took a phenomenological approach and enlisted its participants using Maximum Variation Sampling. The information which was gathered was analysed using Qualitative Content Analysis. The findings of the study revealed that cooperatives of Sesheke District are not involved in any enterprising activity. This is attributed to internal and external barriers towards the enterprising of cooperatives. To overcome these barriers, the study provided policy recommendations and suggested areas for future research.