At a time in education where restrictive pedagogical 'what works' approaches often require teachers to state with some certainty and conviction what 'by the end of the lesson students will understand', there is a need for restatements of pedagogical risk taking and for teachers to find spaces and opportunities for committing to more engaging and enlivening teaching approaches. In drawing on selected works by John Dewey, the paper outlines how pragmatic informed teaching approaches can be conceptualized for contemporary education. The paper pursues this approach by considering pragmatism in relation to propositions and problem solving and learning transactions in relation to habits. Thereafter, by way of exemplifying calculated pedagogical risk taking, the paper then provides applied practical examples of how the broad area of Health and Physical Education (HPE) can become a site for enhanced engagement through pragmatic-informed active learning approaches.