Digitalisation of society is a trend that increasingly impacts various sectors of society like healthcare, education, finance, and government. This digitalisation does not only create new technological developments but also impacts society and its traditional structure, institutions, and organizations. As technology and society intertwine increasingly, it becomes a challenge to address future problems facing individuals, organisations, and society at large, as these problems inevitably become complex in an increasing pace. Wickedly, even specifying and recognising such so-called socio-technical problems become difficult due to the fading borders among cause-and-effect relationships. Specifying and addressing these socio-technical problems will be a great challenge ahead of us in 2030. Addressing this challenge will require innovative approaches that aim at creating an acceptable balance among (contending) values like functionality, economics, ethics, and democracy. In this contribution we motivate adopting a fine mix of designerly approaches and traditional approaches (like engineering) in order to address the uncertainty inherent in socio-technical problems while making maximum use of the existing certainties (i.e., deterministic relationships). Further, we suggest a couple of directions for Rotterdam University of Applied Sciences to appropriately embed cyber-social studies into its fabric and to adequately prepare its future graduates so that they can meet the challenges of designing and realizing cyber-social systems in the future.