Livelihood diversification is integral in increasing household resilience against shocks in the Global South. The study examines the motives and constraints to livelihood diversification. Participants were purposively selected from Springrange, Rocksdale and Fox farms. The results show that diversification of livelihoods is used as an adaptive strategy to respond to long-term reduction in purchasing power parity resulting from climatic and non-climatic factors. However, smallholders struggle to construct productive strategies to diversify their portfolios because of prodigious socioeconomic and financial odds. There is need for development practitioners to stabilise land tenure and scale up access to credit and markets.