Austerity politics in Britain are edging towards compressed learning and teaching identities, driven by competition for resources and normative standards. Policy changes since 2010 have impacted particularly on the arts, and have had an adverse effect on cultural diversity across society. This situation has international resonance for those encountering protectionist reactions to globalisation. Practitioners in creative fields face dilemmas of agency, as they seek to maintain the presence of their roles, and ability to make choices. This paper focuses on how practitioners in post-compulsory art and design and gallery education challenge hegemonic constructions of the self through practice. It reflects on Herne's research of relational differences between teachers and gallery educators, raising points for connective interventions as boundary work. A comparative lens draws upon theories of agency to support critically engaged practice. Empirical data is investigated through Sartre's concept of free will, and Foucauldian negotiations of autonomy.