In 2013–14 a change in assessment criteria percentage weightings on the BA Stage Management and Technical Theatre course at East 15 Acting School was implemented – a course taught mainly through authentic learning processes. This change, coupled with the increase in emphasis on reflective processes in higher education in general, highlighted that students not only on this course but also more widely need to be able to articulate their learning more rigorously than before through more comprehensively written self-evaluations. Through a discussion of critical thinking and reflection and instinctively applying Art and Design pedagogies to teaching on what is traditionally considered to be a vocational course, this article charts an experimental case study following students on the Costume Pathway, hoping to improve their ability in this area. The aim was to develop the self-awareness and analytical and reflective thinking involved in evaluating personal working practices to a high standard in order to improve the written communication thereof. Therefore, this article is also a reflection on how a thorough understanding from educators of what self-evaluation demands of students can enrich student learning experiences and develop transferable skills to produce industry-ready and life-ready graduates.