Engaresero, located on Maasailand in Northern Tanzania, has been in the last few years a good example of the rapid increase of global connectivity and the emergent possibilities arising from being connected to varied social geographies simultaneously. Based on ethnographic research in Engaresero, this thesis examines the engagements of Maasai youth in these varied social geographies. Whether it is the local pastoral rhythm and social order, the national education system or tourism activities, these competing systems each hold their set of expectations and opportunities. By looking at hairstyles, mobile phone usage, vernacular expressions and the creation of ethnographic content for tourists, this paper describes the heterogeneous trajectories emerging from these superimposed systems and structures of authorities. Maasai youth has developed numerous strategies to align expectations with their own aspirations. Their skillful navigation involves intergenerational dialogues that leads to the indigenization of modernity, and boundary work, which enables sustaining competing authorities in order to maintain harmonious relationships. This future-making process of new generations shows fluidity and self-reflexivity and this thesis suggests that it is also historically contingent to the ongoing pressures over the pastoralist lifestyle, land and the idea of being Maasai. The historical plight of oppressive colonial and other dominant powers have shaped this capacity to negotiate competing authorities, and this includes anthropological theories and representations. Reflecting on positionality and land struggles, this thesis questions the anthropological tendency to critique notions, such as “Maasai culture,” at the risk of diminishing the local discourse and commitment to cultural reproduction. Instead, it proposes adopting a similar fluidity in anthropological considerations of cultural representation in order to take seriously the everyday struggles to maintain self-determination in Maasailand.