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This article is an attempt to explore some thoughts regarding how different kinds and levels of expectation might (re)construct being in music education. The philosophical lenses through which this is analysed consist of a combination of a Deweyan pragmatism, the possibilistic parts of the philosophy of the Norwegian philosopher Arne Næss who draws on Spinoza and finally parts of the philosophy of Deleuze & Guettari. A claim made in the article is that it is important in arts educationto challenge the expected and for the world to be created in an eternally wide, and at the same time claustrophobically narrow set of pathways to experience. To learn a communicative art could in other words imply to learn how to consciously adapt to conventions and expectations of musical parameters and at the same time break with them in ways which are functional in aesthetic communication. An important task in arts education must therefore be to train and develop the skill to imagine as rich a web of possible outcomes to any musical situation at the same time as being aware of the conventions that are at stake and their expected uses in order to understand as well as to play with them. That way music education can help pupils become interesting musicians, composers and listeners who are also critical, creative and happy. As an added benefit, these kinds of possibilistic skills, attitudes and modes might actually be beneficial for both learner and society in most parts of life.