If the Brexit referendum, election of Trump, and the rise of right-wing populism suggest anything, it is that our social and political relationships are in dire straits and that we need to rebuild these on different foundations than our current neo-liberal political-economic system. However, there does not seem to be a widespread understanding of what such foundations might look like or what it takes to bring them into being. In this paper I analyse the practices and philosophy of Tree House Liverpool, a community organisation committed to ‘connecting’ people to themselves, others and their environment. Based on the findings of my ongoing action research with them, I demonstrate how they create enabling environments in which people gain greater appreciative understanding of their capacities and relationships as well as what impact this has had on participants and the local community. Drawing on the work of Mary Follett and others about transforming social and political systems in-between people, I will argue that Tree House embodies a relational philosophy which has great potential to transform disintegrated social networks, weak democratic systems, and dysfunctional public services. But as achieving such transformations—ranging from the personal to the systemic level—is hard and messy, I also offer critical reflections on the challenges involved with ‘connecting’ in our current divisive, fragmented, and unequal system.