Personal dilemmas are inspiring phenomena, which can stimulate design creativity and reflection on users’ goals and values. This paper aims to provide an overview of the main challenges involved in Dilemma-Driven Design (DDD). We first introduce three main activities performed when designing with dilemmas: Identifying dilemmas (discovery), selecting a target dilemma (definition), and generating ideas to address the selected dilemma (application). Next, we present a design case in which thirty novice designers responded to a project briefing in three consecutive workshops. Their experiences were evaluated through a questionnaire and a group discussion, resulting in an overview of five challenges involved in designing with dilemmas and recommendations on how to tackle each challenge. Based on our findings, we discuss how DDD is positioned as an emerging, conflict-inspired design approach. Altogether, this paper acts as an ‘introductory course’ on DDD.@en