In this chapter, I describe some of the key constructs of the cultural preparedness framework. I discuss human learning and its relation to work and career development under the rubric of cultural learning, leading to a description of the emergence of a cultural preparedness equilibrium. The acculturative effects of global trends such as financialisation and technological developments altering this equilibrium are presented, highlighting the possibility that the experience of this equilibrium varies across cultures and influences engagement with work, livelihood and career. The discussion interrogates the relatively recent idea of career against the ancient reality of livelihood. A case study of enculturated work roles from the Republic of Maldives is used to illustrate the dynamics of cultural preparedness and the emergence of a viable, new equilibrium.