This book interrogates Immanuel Kant’s work through his studies on anthropology and formulations of the imagination and does so with three tasks in mind. The first task is to investigate the way in which Kant theorises the complexity of our phenomenological existence, which is an enduring pre-occupation throughout his work. This reading of his anthropological studies is accompanied by a second task – to investigate the way in which Kant posits an ‘I’ of the phenomenological subject, that is, capacities for understanding, reasoning and imagining. This second task emphasises the importance of the faculty of the imagination as the central, unacknowledged pivot around which his work revolves. The third task of the book is to explore Kant’s notion of freedom, or in following Kant’s own terminology closely, what is termed here a ‘blurred sketch’, which he simultaneously establishes on transcendental grounds and pluralises. This blurred sketch is central to Kant’s programme and his claim of Enlightenment as the release from self-incurred tutelage. His enduring question is: what is freedom? For Kant, two other questions flow from this one: who are we? What do we create?