This article introduces and explains the concept of the "paradox of education" for capturing the polarity between autonomy and heteronomy in education. The paradox of education is an essential part of the curriculum and, if not under control, manifests itself in the discrepancy between the teaching process, its objectives and evaluation of its outputs. Especially sensitive to the paradox of education are all disciplines that emphasise students' creative expression. In the text expression and its cultural context – expressivity – are characterised as an experimental field for the investigation and management of the tension between autonomy and heteronomy in education. The characteristics of expression are derived from Goodman's (1976) concept of symbolisation as a type of expression, but is developed with regard to the relationship between subject and cultural context and in relation to Searle's (2004) differentiation of first and third person ontology. The interpretation leads to the formulation of a theoretical model of subjectivity in the context of culture in education. The theoretical model of subjectivity shall contribute to the development of a comprehensive approach to the curriculum, which with respect to the paradox of education balances the autonomy of the pupil together with a heteronomous system of cultural rules. The model is illustrated in a case study of voice education. The interpretation supports the educational efforts that lead to a holistic approach to assessment in the expressive disciplines with emphasis on the quality of the educational process, not only on the evaluation of outcomes.