This paper questions the bounds of hegemonic knowledge production focusing on how student learning at the university level is a site to re-imagine knowledge produced in the Global South/Majority. It argues that there are transformational approaches to teaching and learning within the Caribbean that need to be centred in global pedagogical practices. The authors reflect on elements of their teaching that rest in creative, formative assessments and demonstrate how student learning is enhanced through exercises that cultivate their agentic power. The paper examines three creative assessment methods: a Reflective Letter to Yourself Essay, a Poster Assignment, and the use of Dramaturgy in a final group project. Through these assignments, the authors demonstrate the importance of prioritizing the necessary salience of the evaluative 'looking out, looking in' process of learning that students undertake. This allows for an enhanced use of creative exercises that challenges reproduction of the colonial as a norm.