Homo academicus, who are we, who do we want to be, and how do others view us? There are many alternative answers to these questions. In this chapter, I explore three different conceptions that not only differ in outlook and underlying assumptions, but also on who counts as Homo academicus. The three are Homo academicus as guild, employment, and attitude to knowledge and learning. As during previous information technology revolutions—writing, paper, printing, penny post, telegraph, copier, e.g.—the present digitisation again poses challenges to the established order, power structures, and conceptions of (worthwhile) knowledge, giving cause to look at the assumptions underpinning and shaping these conceptions. Again, the role of the academy is in transition.Entering a road towards Homo academicus-ship may be motivated by a range of desires: the search for truth or justified true belief; a longing for becoming an authority—or merely to be accepted into the circles where those one views as authorities reside and act; making a career in a structure with a seemingly clear hierarchy—or merely making a living; a passion for a topic; a wish for intellectual challenges—or merely intellectual conversations …. These desires can be met to differing degrees and in different forms depending on the conception of Homo academicus. And the surrounding world provides support, funding, admiration, challenges, and disdain partly based on which conception(s) surrounding actors hold.How these three conceptions and their underlying assumptions interact, challenge, and are challenged by each other and by trends in the societies of which they form parts, is the object of this chapter examining current transitions.