In light of the large burden of chronic disease and the low rates of long-term treatment adherence contributing to high rates of morbidity and mortality worldwide, this paper contributes to better understanding the particular kind of challenge that living with chronic illness and adhering to long-term treatment can imply. Both literature on the concept of chronic disease and the experience of illness suggest going outside specific diagnostic categories to better understand the problem of adherence. After introducing the distinction of a thin understanding of chronicity—merely as long duration—and a thick one—chronicity in a phenomenological sense, this paper analyses academic literature on the experience of illness and specifies it to the case of chronic diseases, introducing an original conceptual framework describing some main challenges arising from the experience of chronic disease. The framework is organised in three dimensions: failing to recover as a failure to belong, being at a loss and breaking-up with oneself. This work suggests a particular subjective state in which struggling to follow long-term treatment may seem understandable and reasonable, offering a phenomenological perspective that feeds into the ethical problems arising in chronic diseases, and shedding light on how to increase adherence without reproducing patterns of disadvantage.