The authors reflect on recent experiences at UN-Habitat and other international organizations to rethink the roles of planning towards larger development goals and to reform planning systems in places most in need of them. They consider the difficulties but ultimate necessity to learn from a variety of contexts and experiences to articulate general orientations for planning and planning reform which can partly transcend context. Within the variety of planning experiences, and the experiences of lack of planning, one can discern principles which can be applied in many contexts, yet those include principles of contextualization and learning. Comparative learning underpins the attempts at finding general principles, and the local application of those principles further triggers processes of learning, including comparative learning. Local and grassroots planning capacity building is vital to locally apply and contextualize international planning guidelines.