In this article, I examine the foundations of design knowledge and how they have been disrupted as the design discipline moves progressively away from industrial production. I consider design knowledge as a collection of different cognitive processes for developing artifacts for the human-made world. Adopting David Kolb's (1984, p.38) definition of learning as “the process whereby knowledge is created through the transformation of experience,” I discuss the change in design knowledge by examining how the characteristics of designed items have changed. Building on theories by Neri Oxman and Richard Buchanan, I identify relevant areas of design practice in which creativity is breaking free from disciplinary silos to flow between physical, digital, metaphysical, and biological layers. I then propose an updated map of the orders of design as a thinking tool and compass. I read the evolutions of design as it enters the Fifth Order of concerns, characterized by the centrality of data both as input and as output to a design process. Today, design deals with relationships and perceptions; it dialogues with people and all species ranging from machines to micro-organisms, all of which actively participate in reaching objectives. Here, design creates conversations to achieve several goals, including engagement, discovery, and decision making. Finally, I propose a shift in the traditional principles of designing, moving away from the idea of perfect solutions and toward learning systems that are good enough for now.