This presentation offers a situated inside perspective of ambiguities in planning practice. The aim is to explore how ambiguities can be made visible and put to work as a resource for practical wisdom in planning practice. A starting point is that planning is a messy, complex activity, involving high uncertainty, conflicting interests and a multitude of actors. Planning is also about making everyday judgements in new and complex situations (Campbell 2012, Healey, 2020). A wise judgement is however not something that the planner obviously possesses but is an ability that demands constant ‘training’ in practice (Håkansson, 2005; Metzger, 2014). While recent planning research highlight frustrations (Zapata, 2021), tensions (Saldert, 2021), dilemmas (Khakee, 2020), ambiguities (Fridlund, 2017, Wiberg, 2018), there is still a lack of research how such phenomenon can come into the light and be utilized in everyday planning, to foster transformation and changed practice. In this article we are interested in how ambiguities can be made visible and put in used in everyday planning practice. Can ambiguities been used as a resource for practical wisdom in ‘messy’ realities, i.e. to judge what is better or worse without losing sight of possible problematic outcomes of what you put in practice? The empirical material is based on autoethnographic writing from the perspective of two researchers that have former been working for a municipality in the metropolitan area of Stockholm.