Limited non-farm opportunities in the rural areas of the developing world, coupled with population growth, means agriculture will continue to play a dominant role as a source of livelihood in these areas. Thus, while rural transformation has dominated recent literature as a way of improving welfare through diversifying into non-farm sectors, improving productivity and resilience to shocks in smallholder agricultural production cannot be downplayed. This is especially so given the changing climatic conditions affecting agricultural production, and thus threatening many livelihoods in rural areas. Farm diversification is an important strategy for creating resilience against climatic shocks in farm production. Using cross-sectional data from northern Namibia, the study assesses the barriers and success factors related to effective crop and livestock enterprises diversification and the effect of these on food security outcomes. A Seemingly Unrelated Regression model is used to assess the joint factors explaining total farm diversification, while a step-wise error correction model is used to evaluate the conditional effect of diversification in each of the two farm enterprises on two measures of food security: food expenditure and dietary diversity. We find that past exposure to climate shocks informs current diversification levels and that access to climate information is a key success factor for both livestock and crop diversification. In terms of food security, greater diversification in either crop or livestock production leads to higher food security outcomes, with neither crop nor livestock diversification showing dominance in affecting food security outcomes. However, an overall higher level of diversification in both livestock and crop enterprises is dominant in explaining food security outcomes.