Planning through processes of "co-creation" has become a priority for practitioners, urban activists, and scientific researchers. However, urban development still shows a close instrumentalism on goal-specific tasks, means, and outcomes despite awareness that planning should enlarge possibilities for social change rather than constrain them. The article explores the dilemmas of planning agency in light of the contemporary need to open spaces for innovative practices. Planning is understood as a paradox; a structural tension between organization and spontaneity. The article provides a detailed profile of three specific dilemmas stemming from this condition. We distinguish and conceptually explore the dilemmas of intervention, regulation, and investment in current practices. The article provides a specific understanding of today’s planning dilemmas, exploring the key notions of "space and time" in the intervention dilemma, "material and procedural norms" in the regulation dilemma, and "risk and income" in the investment dilemma. We suggest that planning practice today needs to make sense of these dilemmas, navigating through their extremes to find new contextualized forms of synthesis.