Rural communities of sub-Saharan Africa are under increasing adaptive pressure resulting from decline in the quality of land resources. To increase food, generate income, and safeguard against risks and shocks, families are engaging in multiple livelihood strategies. This study was conducted to: 1) evaluate livelihood strategies; 2) examine the dynamic diversification process in the agrarian and non-agrarian continuum; and 3) investigate how type and availability of assets influences choice of a livelihood strategy. Results from our investigation in western Kenya suggest that as land is subjected to degradation, there is a shift in the type of assets that families can draw upon. Among the Luo, collision between deeply embedded cultural beliefs and access to land, is leading to a shift from farming to non-farming activities. They are heavily reliant on human labor to make a living hence becoming less resilient, and more vulnerable to existing and emerging risks and shocks. The overriding scenario is escalated land degradation, increased poverty levels, and a failed social support system. Asset diversification and intensification processes among the Kipsigis are closely intertwined with rapid social-cultural change and strong bonding and bridging ties. They are involved in an asset-led intensification and diversification strategies. Overall, our findings suggest that the ability to make a meaningful livelihood is dependent not only on the quality and quantity of assets that an individual household possesses, but also having capabilities to use and transform the assets as well.