The design studio is a unique environment typically situated at the center of design education. This study explores the transition from a conventional design studio to a real-life design context and examines the changes in the design process adopted by students in such a setting. For this study, 25 interior design undergraduates were included through a convenience sampling technique. The students were exposed to a real-life context where they could engage with contextual scenarios and collaborate with end users whom they encountered in a workplace setting. In the architectural design process, end users are the individuals who will benefit from the design once it has been constructed. The Manin Market in Peliyagoda, Sri Lanka, was selected as the real-life context for this study. Action research methodology was employed, with data collected through naturalistic observation, focus group interviews, and photographs. The data were analysed by using a six-phased thematic analysis. The findings reveal the emergence of the empathizing phase as a critical component, interwoven with all major design thinking phases. Additionally, the study identifies the use of information and communication technology (ICT) tools as essential mediums for design communication throughout the students’ design process in a real-life context.