Building on ethnographic fieldwork among militant, urban youth in Bissau, Guinea-Bissau, this article illuminates how young men in the city actively engage in conflict in order to improve their lives and prospects. The article shows how mobilizing is seen as a move toward a reduction of hardship and the possibility of fulfilling one’s social potential. Rather than looking at what people see themselves as having to fight against—the last decades of war in Bissau being remarkably void of ideological standpoints and collective visions of dangerous Others (Vigh 2009)—the article looks at the visions of better futures that transcend conflict engagement and wartime suffering for young militiamen. It clarifies the positive prospects that are expected to lie beyond the known horrors of war. Though conflict and warfare may provide strange points of departure for talking about well-being, imaginaries of happiness stand out from a background of hardship and are talked about in both a quite concrete way, as a lack of insecurity, as well as in an abstract way, as realization of social being. However, for most of the people I talk to, happiness remains elusive and evades their desperate attempts to grasp it. It appears, as such, simultaneously to be what life is most profoundly about, as well as the dimension of it that constantly seems to avoid capture.