It Is Simple, It Is Complicated

History is not a strictly linear process; our progress as society is one full of contradictions. This we have to bear in mind when trying to find answers to pressing challenges related to and even caused by the digital transformation. In this chapter, we reflect on contradictory aspects of Digital Humanism, which is an approach to foster the control and the design of digital infrastructure in accordance with human values and needs. Seemingly simple solutions turn out to be highly complex when looking at them more closely. Focusing on some key aspects as (non-exhaustive) examples of the simple/complicated dilemma, we argue that, in the end, political answers are required.