The work of teachers is regularly quizzed and questioned. The responses called for commonly implicate assessment, as this provides answers about learning, which many believe directly translate into answers about teaching. We question teaching differently, beginning with the basic what, how and who questions, while also posing the why question: 'Why do you teach?' This enables us to draw student engagement and achievement of intended learning outcomes into closer relation via an improved integration of teaching and assessing. In our exploration of these questions, we engage with aspects of Vygotsky's and Dewey's educational theories, highlighting correspondences and differences. Our aim is to illuminate convergence around two key concepts: perezhivanies and occupations. Both speak to recognition of a unit of life as a unity of person in context that can function as a unit of study in educational terms. We bring this theoretical convergence to teaching practice via creative learning units. This unit planning framework offers a coherent approach that entwines student engagement and the achievement of intended learning outcomes.