This commentary centres on the questionhow can we further develop the relationship between planning practice and academia? This question has been one of the central pillars of planning scholarship over several decades (Krumholz, 1986), but many would agree that previous arguments have not yet been taken far enough in action. Drawing upon the web of existing arguments for a closer theory-practice relationship, our intent is to unpack additional experiential dimensions of this overarching question that need to be understood in a relational manner. Any such understanding should be placed in the context of non-collaborative pressures in both practice and academia, and open new pathways for understanding structural barriers to their closer collaboration. To this end, we will start by explaining the demanding contexts that planning now faces. We then reflect on how planning in itself is a complex procedural practice. The central premise here is that planning is institutional, but ultimately a human action at its core, that is characterised by psychosocial dynamics that need to be accounted for. Advancing this argument, we will acknowledge previous reflections on psychosocial aspects of planners' everyday. Arguing from inference, we conclude that furthering collaboration between practice and academia will require understanding the diverse and dynamic experiences of planners whose everyday practices are embedded within complex psychosocial processes, distributed across various social networks and time. Bearing in mind these deeper understandings of planning as a complex and deeply emotional practice, we reflect on potential actions for developing co-creation processes that engage both practice and academia. Of Wicked Problems and Planning Complexities In light of the recent Intergovernmental Panel on Climate Change report (IPCC, 2019), humanity has to face the fact that wicked problems, highlighted decades ago (Rittel & Webber, 1973), still hang above us like Damocles' sword. We live on a limited planet, where resources are often scarce compared to current human needs (Raworth, 2012). Moreover, natural, infrastructural, and technological systems have a large number of interdependent relations, resulting in a non-linear and rapidly changing reality (de Roo & Silva, 2010; Sengupta, Rauws, & de Roo, 2016). At the centre of this existential understanding is the idea that multidimensional human ends are not static and fully defined, and that various groups have different needs, over time. Thus, transitions out of our unsustainable lifestyles require not only changes in the built environment and technological systems but, most importantly, in our behaviours and societal values (Geels, Sovacool, Schwanen, & Sorrell, 2017). However, this state of irreducibly high