In this compilation, the authors present the results of a research project that investigates how understanding the relationship between culture, employment and education can help Tanzania’s young people to secure jobs, survive in the creative workforce and have a prosperous future.The authors define situation specificity, showing that the previous discussions have been overly simplistic. It is suggested that situation specificity is important in at least three ways: practice and theory-practice transfer, methodological issues including generalization and biases, and dispositions as goals of educational intervention.Next, it is proposed that an ethnomathematics curriculum helps students to demonstrate effective mathematical processes as they reason, solve problems, communicate ideas, choose appropriate representations through the development of mathematical practices, and recognize its connections with STEM disciplines. The authors’ work, in relation to STEM, is based on the Trivium Curriculum for Mathematics and Ethnomodelling, which provides communicative, analytical, and technological tools as well as the development of emic, etic, and dialogic approaches that are necessary for the development of the school curricula.The penultimate chapter provides an overview of the role of higher education institutions in graduates’ entrepreneurship knowledge acquisition in Tanzania. Unemployment problems faced by recent graduates in the country are highlighted and linked to the diffusion of entrepreneurship into non-business academic programs.In the closing chapter, the authors argue the need for a paradigm shift from the current domain focused curriculum (or semi-functional curriculum) to one that is really functional for acquiring of relevant knowledge and skills. Education should take place within authentic contextual learning environments, where complexity may be unpacked gradually through continuous exposure and habituation of expected responses.