A dynamic relationship exists between land and livelihoods that is rapidly transforming the lives of people of Awach River catchment, western Kenya albeit in different directions. Among the Luo people negative livelihood capitals synergies exist, that are triggering downward spiral of the community. The negative interaction is making them unable to withstand internal and external shocks. As the land continues to degrade, the people lack the needed will power, self confidence and determination to break away from deeply embedded cultural practices and reorganize their livelihood assets into productive systems. Instead, they are escaping from their village problems, and in turn, their land and livelihoods are collapsing. The end result is escalating land degradation and increasing unsustainable livelihoods. On the other hand, the Kipsigis are experiencing positive capital synergies that enable them to adapt and utilize a range of capital management strategies. They are able to take advantage of internally changing capitals and external opportunities to build a healthy and resilient agrarian community associated with asset intensification and diversification.