Having set his anthropologically perceived parameters for positing ‘a release from self-incurred tutelage’ Kant posits that transcendental critique occurs through the mobilisation of categories and concepts that function according to the rules of the faculty of understanding. Yet, the Critique of Pure Reason conceals a nugget that is often overlooked or underexplored. This nugget is Kant’s ruminations on the productive imagination, especially when he terms its products schemata and figurations. In the A and B Deductions in the Critique of Pure Reason Kant speaks of the imagination as functional schemata and as a non-functional figurative synthesis. Figurative synthesis is Kant’s insightful and fertile attempt to capture what the indeterminate, unknowable, even unfathomable and spontaneous aspect of creativity itself, the site, activity and power of which he names as the productive imagination. The transcendental moment in Kant’s work is best described as the creation of blurred sketches that encapsulates our capacity to invent or compose concepts, categories, ideas, think, create, participate in and critique social arrangements and relational forms. The interaction between our difficult selves, the productive-schematicising imagination, the unsociable sociability requires the creation of blurred sketches, especially those of freedom, through which evaluations, judgements, and responsibilities can be created and practised.