This paper presents the case studies of Compassionate Bruges and Herzele, as experienced in the role of a project leader/facilitator. Two cities want to grow more solidarity and more carefulness for their citizens as an answer to social bitterness, coldness and isolation. Two PhD students search for an answer to the question ‘how can we develop and foster a civic approach that is complementary to institutional health care, improving the quality of life in situations of severe illness, dying and grieving?’. And to the question ‘how can we invite people to think and act differently to realise this social change?’. The uniqueness of this testimonial lies in the top-down approach that was chosen to implement the compassionate city as well as the compassionate community aspect of this project. This is unlike a lot of international examples of compassionate community projects that are rather driven by an individual ‘sponsor’ or grassroots initiatives. In the top-down approach, we bring together partners like schools, employers, life stance groups,… In the bottom-up approach we work with civil society organisations and key figures in local networks. We aim at developing a compassionate community in Bruges Sint-Kruis as well as in Herzele-Centre. We will give an overview of how the project was conceived and how both cities evolved in their own way, driven by local differences in policy making, social network dynamics and the people involved. We will present the tensions that emerged and what we did to try and manage these tensions, as well as to manage the complexity of the global context in which these projects deployed. Since some of our interventions proved to be more successful than others, we will conclude with some learnings and reflections and a brief presentation of the ‘Navigation Triangle’ framework. This framework is the synthesis of the levers we experienced to be crucial to understand and use in the process of leading cultural change in a complex environment. This framework might inspire project leaders and ...