Computing is becoming exponentially more pervasive, and so-called process of ``Digital Transformation'' is but starting. As computers become ever more relevant, our societies will need computing professionals that are well-equipped to face the many challenges their own discipline amplified. The education of computer scientists, so far, mostly focused on equipping them with technical skills. Society and academia, however, are increasingly recognising computing as a field where disciplines collide and intersect. An example that we investigate is that of Innovation and Entrepreneurship (I&E), a field that has often be used to equip computer science students with soft skills and non-technical competences. Computer science faces some unique problems, among which a lower student interest for non-technical subjects, and a constant process of epistemic and technological obsolescence. This thesis showcases some experiences that aim to address these challenges, going towards (re)connecting the Humans and Machines participating in computer science education with the needs of the World of today and tomorrow. Our work combines some theoretical reflections with pedagogical experiments, to ensure that our work has at the same time descriptive power and empirical validation. To aid teachers and learners in the change process, these experiments share a pedagogical approach rooted on Active Learning, ranging from Challenge-Based Learning to Peer Education, to custom-tailored teaching methodologies. In designing each experiment, we start by asking ourselves: how is what we want to teach practiced in the real world? Theoretically, this thesis contributes to the state of the art by conducting a horizontal exploration of how computer science education can enter an age ever more dominated by so-called ambiguity. Methodologically, we propose lightweight techniques for qualitative measurement that are rigorous, but introduce little methodological burden, emphasising our work's reflective and exploratory dimension. Our work aims to show how, using the same broad design process, courses can be flexibly adapted to fit an ever-changing world, including significant disruptions such as the transition to online education.