This book provides concrete pedagogical suggestions for teaching the translation of cultural items, including so-called ‘untranslatables’. It is underpinned by sound educational theory and empirical data, and sheds light onto a complex and under-researched pedagogical area by testing the effectiveness of established teaching approaches. The book adds to the repertoire of translation pedagogy by presenting elements of learner psychology, positive psychology and humanistic education as vital parts of translator education, in particular when engaging with the great challenge posed by the translation of cultural elements and learner barriers and anxieties. The book argues that fostering knowledge building and training research skills will contribute to developing resilience and the ability to strategically engage with the challenge of translating cultural items in a holistic manner, i.e. as contributors to a text’s achievement. At the same time, it cautions educators against uncritical and exclusive subscription to specific pedagogical paradigms. The book is of relevance to translation teachers and scholars, as well those engaging in wider educational research revolving around complexity and threshold concepts. It is of interest to translation students who would like to explore new perspectives in the area of practical translation of cultural items.