This paper explores the intersection of everyday urbanism and digitalization, drawing insights from a multidisciplinary workshop fostering critical dialogue and shaping research agendas. It extends the discourse beyond practical applications, questioning societal and urban impacts and what it means to be human. The discussion highlights the evolving digital-physical relationship, the paradox of digital platforms in human interaction, emerging city management and participatory ecosystems in data era, and the validation of digital realities. The paper concludes that challenge for urban policy and research is to harness digital technology for sustainable ways of being, ensuring a more connected rather than fragmented world.