This project is a study case of Melbourne that addresses the complex process of sustainable transitions in mobility. The study explores Melbourne’s heavy, car-focused socio-technical regime and people’s challenges and barriers to bicycle commuting. It presents navigational pathways as a method to look for cracks in the existing regime while building new networks to support and encourage the sustainable transition. The project addresses stress as the major deterrent of cycling and explores how to design a safer, lower-stress and more enjoyable bicycle commuting practice. The project proposes Comfort Cycling app to lower-stress cycling experience as a tool to disrupt the existing regime, address car-based practices and involve relevant actors in the network. The main findings of the project suggest that assigning new values to cycling, building new networks and designing a new cycling practice are the basis of enabling the sustainable transitions.