This paper features a personal summary of inherited and en-route acquired experiences along the particular trajectory of Ademir Volić’s career. It seeks to further examine the fundamental question of choice in choosing the appropriate path to "creative freedom" regardless of context. Today, the context is one of unprecedented global geopolitical changes, pressing planetary sustainability issues, and, within the architectural sphere, the ongoing essential debate regarding the societal roles of urban planning and architecture and their consequences. What follows is a transition from hypothetical scenarios to lived reality.