This article describes a sequence of design research projects, some exploratory others more formal, on the teaching of modelling and the analysis of modelling skills. The initial motivation was the author's observation that the teaching of applied mathematics in UK high schools and universities involved no active modelling by students, but was entirely focused on their learning standards models of a restricted range of phenomena, largely from Newtonian mechanics. This did not develop the numeracy/mathematical literacy that was so clearly important for future citizens. Early explorations started with modelling workshops with high school teachers and mathematics undergraduates, observed and analysed--in some case using video. The theoretical basis of this work has been essentially heuristic, though the Shell Centre studies included, for example, a detailed analysis of formulation processes that has not, as so often, been directly replicated. Recent work has focused on developing a formative assessment approach to teaching modelling that has proved both successful and popular. Finally, the system-level challenges in trying to establish modelling as an integral part of mathematics curricula are briefly discussed.