Effective poverty reduction in Africa requires enabling more smallholder farmers to move from subsistence farming to a more entrepreneurial fashion of farming. Earlier studies showed that smallholders are constrained in doing so because of lack of incentives, high risks, production problems and lack of an entrepreneurial mindset. Deterioration and improvement of the natural resource base impact these constraints. In this paper we not only focus on soil fertility decline and the available measures to combat this decline but also on the reasons smallholders have for applying them or not. 94% of the 232 smallholders we interviewed in this study report a decline of their soil fertility. During interviews smallholders in northern Ghana gave their reasons for (not) applying the soil fertility enhancing measures manure use, use of household waste, compost making, use of mineral fertilizer, fallowing, improved fallow, use of cover crops, use of human excreta, crop rotation, anti-erosion measures, and non-burning practices. In this paper we evaluate the constraints of implementation of the different soil improvement measures. The most striking conclusion is that implementation of these measures is restricted by the same constraints context that restricts smallholder entrepreneurship in the first place. We therefore argue that, to develop subsistence farmers into more entrepreneurial farmers, support programs are needed that address the entire constraints context for smallholder farmers.