The paper develops and addresses a major challenge for therapeutic conceptions of philosophy of the sort increasingly attributed to Wittgenstein. To be substantive and relevant, such conceptions have to identify “diseases of the understanding” from which philosophers suffer, and to explain why these “diseases” need to be cured in order to resolve or overcome important philosophical problems. The paper addresses this challenge in three steps: With the help of findings and concepts from cognitive linguistics and cognitive psychology, it redevelops the Wittgensteinian notion of “philosophical pictures.” Through a case study on seminal versions of familiar mind-body problems, it examines how such pictures shape philosophical reflection and generate ill-motivated but captivating problems. Third, it shows that philosophical pictures are constitutive of “diseases of the understanding,” in a quite strict sense of the term. On this basis, the paper explains when and why philosophical therapy is required.