The motive for this research is to contribute to the development of a resilient city, specifically to the transition to a sustainable car system. Road removal or road reallocation can be considered as a means to induce reduced demand for car mobility. Yet, the implementation of these measures can count on resistance. This resistance is negatively influencing the plan development and decision making required for the transition. The aim of this research was to gain insight in and obtain knowledge on the social feasibility of the implementation of measures inducing reduced demand, to be able to enhance this social feasibility and so to enable the transition. The main research question is: “How to enhance the social feasibility of the implementation of measures inducing reduced demand in car mobility?” To answer this question not only the practice of implementing measures inducing reduced demand has been researched, but also theory has been researched to gain insights on an abstract level which can contribute to answering the main research question. The aim of the research in practice was to gain insight in various aspects of social feasibility for road closure projects in Amsterdam. For this a case study was performed. The case study entailed of an combination of research methods: interviews with professionals, a survey and a reflection group as well as some methods to gain neighbourhood specific knowledge like socio demographics and traffic intensities. The theoretical research originates from the idea to reflect on the way how transitions, like the one to a sustainable car system, and innovations, such as road removal, come about. For this reflection literature in the realm of Actor Network Theory and Complex Systems Theory was reviewed. From this review two concepts were derived, namely ambiguity and uncertainty. These concepts were explored by interviewing innovators. To them it was asked: How to handle ambiguity and uncertainty in order to be able to innovate? It can be concluded, based on the analysis of the surveys, the interviews and the results of the reflection group, that social feasibility of measures is heavily impacted by ambiguity and uncertainty. Yet, from the reflection on theory, it can be concluded that embracing ambiguity and uncertainty will enhance social feasibility of measures. To achieve this, the professionals and innovators recommend the application of stakeholder involvement and experiments.