This paper questions whether are we able to foster uncertainty and ambiguity within higher education arts programmes, specifically alongside current institutional demands and embedded pedagogies. If not, then what effect does this have on current dance graduates? I attend to these questions through critical reflections upon my work as a pedagogue, specifically reflecting upon a series of artistic choreographic projects working in collaboration with recent dance graduates. During these choreographic projects, my interactions with the graduates illuminated their struggle to operate within ambiguous creative spaces outside of institutional environments. This struggle manifest in turbulent working relationships and highlighted perceived contradictions or "gaps" between what creative arts education attempts to teach, how it is taught within the institution, and what graduates demonstrate within professional creative practice. Through a recognition and critique of these "gaps", I question whether it is possible to actively work within these "messy" spaces, to chase the ambiguities present, in order to foster sustainable dance graduates that can work more visibly alongside academics and professionals to shape the current dance landscape.