The decision-making processes of small-scale farmers are frequently ignored in discussions about food security in sub-Saharan Africa. Consequently, policies intended to improve land productivity often fail or produce ambiguous results regarding their efficacy. As rainfall becomes increasingly unpredictable, and as productive land becomes increasingly scarce, we must rethink how to enable more efficient land management strategies, with greater emphasis on enabling the individuals who manage the land. In this paper, we study two different groups of farmers in Kenya: traditional rural farmers and an emerging class called the 'telephone farmer.' They face different operational constraints but share the common goal of deriving profits from agriculture. We develop eight profiles that attempt to explain what production actions farmers are likely to take and why. Our findings suggest that better characterization of the small-scale farming landscape can help to shape policies and incentives in ways that will amplify farmer priorities to increase land productivity and ultimately improve the prospects for food security.