This research was done in southern Mali to understand and support the ability of smallholders to cope with variation in weather and economic conditions to sustain their livelihoods. I found that farmers produced cotton and cereals for several reasons, including to diversify the sources and timing of income, to secure access to credit and agrochemicals and to strike a balance between the security and flexibility. Farms of different resources were equally exposed to weather change, but with different sensitivity and adaptive capacity. A “cotton crisis” induced by the COVID-19 pandemic resulted in large reduction of cotton area with limited access to fertilizer inputs without negative effect on the yields of cereals and food self-sufficiency, with different implications for farms of different resources. Lastly, I developed a farm management approach and a support tool for informed decision-making to cope with unanticipated circumstances.