This article reports on a learning design project that encourages the creative (re)use of popular literature as educational materials by bringing together scholars and insights from diverse disciplines to engage learners and build the human(ising) skills needed in health professions. A capable health professional is one who has technical competence, interpersonal and critical thinking skills. They need to be able to understand and cope with complexity and ambiguity, human diversity, and the reality that people differ in the factors that assist them to become ready for change and stay well. Critics of the direction that health education has taken to prepare graduates indicate that there is a preference for technical skill development, whilst overlooking craft knowledge. Students still need to learn bio-technological knowledge, but they also need to understand the multiple social, cultural, and environmental contexts that can impact on a person’s journey of change in health. The project reported in this paper outlines a novel process of engagement in case-based learning. Particular illness memoirs have been selected, and important plot lines within the stories extracted to depict variations of a person’s health journey. A book club process, familiar to most people as a fun way to engage in multiple readings and perceptions about the merit of a text, is the medium through which these excerpts are discussed. Thus, the materials act as triggers, not solely for inquiry, but for the development of empathy and understanding of different contexts, which are then aligned to clinical strategies assisting students to develop technical skills and interpersonal abilities.