Planning and sustainability are extremely challenging concepts in the current development discourse. This paper argues that besides being challenging, they are also closely related in a complementary fashion. To achieve holistic sustainability, efficient planning is inevitable. With this understanding, the article explores ways in which planning and sustainability are intricately linked. The focus is mainly on how planning can enhance the chances of achieving sustainability. Following this, a set of criteria to gauge the efficacy of contemporary plans with regard to achieving sustainability is suggested. A list of substantive and process criteria is presented which plans must adhere to, if transition to a sustainable pattern of existence is to be successfully achieved.