The need for a sustainable transformation of the transport system has been known for decades, but it has proven challenging to translate insights and policy goals into action. One of the explanations is that prevailing conventional and techno-rationalist approaches in transport planning do not help to answer the inherently political and uncertain question of what a sustainable system for mobility and access might look like. This chapter aims to provide perspectives on ways forward for developing transport planning into an arena where transformation-orientated ideas, i.e., ideas related to sweeping change and the consideration of other possible mobility futures, can be accommodated and explored. In the chapter, which builds on empirical material from Swedish transport planning at the national level, the concepts of the political and strife are used to discuss the critical role of planners to navigate wicked planning situations and work productively with conflicts in strategic planning situations.