One of the central tenets of 'middle schooling' has been a commitment to provide a curriculum that is 'relevant' or 'connected' to student lifeworlds. Examples of this sentiment can be found in the Queensland Productive Pedagogies (connectedness), the multi-literacies (situated practice) and the assertion of constructivism in the South Australian SACSA Framework. But, as the Redesigning Pedagogies in the North project is finding-'easier said that done'. What this paper will to address is the possibility of actually pursuing 'connectedness' as both a curriculum and pedagogical challenge. As such the paper will take up these two interrelated questions: how can teachers design curriculum that connects with student lifeworlds? And what are the challenges for pedagogy? This paper will argue for 'strong' versions of connectedness and provide examples of what this might look like in practice.