This study aims to contribute to the ongoing scholarly conversation about education throughthe lenses of the German philosophy of Bildung and the American philosophy of pragmatism. Moreconcretely, in this article, the two philosophies are represented by the traditions of critical-constructiveDidaktik, based on Wolfgang Klafki’s work, and transactional realism, based on John Dewey’s. Againstthe background of the widespread outcomes-based modes of education today, the authors seek to shedlight on the necessary reconceptualization of schooling and teaching and to explore the possibilitiesfor constructive routes forward for curriculum theorizing. They outline the aspects of knowledgeand the learning concepts that the two philosophies share and those about which they differ. Theauthors also analyze the consequences that these similarities and differences have for the educationalapproaches of critical-constructive Didaktik and transactional realism. Finally, the authors present anempirical example from a Swedish year-eight classroom, drawing conclusions based on their findingsand considering corresponding implications about the two traditions’ potential to contribute to anunderstanding of teaching as a pedagogical responsibility.