The present study explores Paul Klee’s philosophical insights within the cosmic and ontopoietic dimensions. It shows how the relationships between the opposites of chaos (disorder) and cosmos (order) establish links with internal experience, imagination, and creative dynamism. Firstly, the paper underlines Klee’s concept of a work of art as an energetic movement and polyphonic plurality of images, rhythms, lines, colours and sounds, and links this to a phenomenological approach to imagination. Secondly, it shows how Klee’s notion of creative dynamics and generative functions relates to Anna-Terese Tymieniecka’s philosophy of cosmic ontopoiesis. Thirdly, it analyses two concepts: the centre and the in-between. Klee’s centre of artistic imagination—the grey point—and formation of the centre of stability, analysed by Gilles Deleuze and Félix Guattari, makes a comparable approach to humanity and art. Life in in-between situations is the human condition as such. In-between people are the cosmic points and, at the same time, centres of creative dynamics that maintain a balance between different milieus. The study aims to show how energetic dynamics flow through human beings, their creations, their imagination, and the cosmos.