As foreseen by visionaries in the 20th century, mastery of the dynamic processes that underpin the acquisition and manipulation of knowledge is quickly becoming a critical capability in the 21st century. Our formal educational systems do not tend to facilitate the development of these capabilities, yet people of all ages are developing them via a variety of digitally-mediated mechanisms. Online games offer one area of exploration for spontaneously-occurring phenomena that represent the natural development of such literacy. This chapter reviews the need for 21st-century skills and illuminates existing digital domains in which these skills develop organically. Peering through the window of the present into the future, we present a view that envisioning change means taking a long look at what is working now, regardless of whether that activity is taking place in a formal setting or within entertainment-based worlds where the skills are mandatory for mastery, but learned incidentally through play.