This paper explores the notion of "productive risk" as a way of understanding how diverse students can become re-makers of landscape architectural design practices and education. We trace the design trajectories of two first-year students at a South African tertiary institution and examine how the students negotiate the risk of drawing on their own experiences and resources in order to access conventionalised disciplinary practices. It is important to recognise students' brought-along resources, but we also need to recognise the risk involved for the students and teachers in drawing on these resources. This risk needs to be seen in the light of a history of colonised education where diverse resources and experiences were often disregarded or devalued. We show how these students contextualise landscape architecture in terms of their own experiences and draw on their resources as prompts to space-making for the imagined users of their designs. We surface the risk in terms of students' experiential resources as well as the use of unusual model-building materials and techniques. The high levels of engagement that these two students demonstrate in their design trajectories reveal the importance of making a connection between diverse contexts and the landscape architectural classroom. We argue that a pedagogy that embraces risk as productive can recognise and validate the rich knowledge, resources and experiences that students bring with them.