This article explores the potential of the concept of ‘dilemma’, as introduced in Mark Bevir and R.A.W. Rhodes’ interpretive political science, to understand and explain change within and beyond political institutions. This article argues that the current conceptualisation of the concept has been underdeveloped and the potential opportunities of using it have been overlooked. The concept of dilemmas must be developed in two directions: first, through a greater linkage with everyday practices and, second, through a greater linkage to the concept of power. To do so, this article draws on insights from the concept of ‘problematisation’ as a way to explain change. This adds more detail to dilemmas by arguing that, while dilemmas pose problems for existing beliefs and webs of belief, they also erect boundaries over what is an acceptable answer or resolution to dilemmas. It is this simple yet key insight that offers an opportunity to further strengthen interpretive political science, and offers much potential for future research on political change.