Introduction: We live amidst the biggest explosion in knowledge in human history. More and more facts emerge, faster and faster, from the activities of researchers. More and more applications of those facts are then transformed into technologies which in turn allow the further emergence of yet more facts. This process is driven by methodological innovation in the production of knowledge that began crystallizing during the Renaissance and hit its stride during the Enlightenment. Set adrift from its traditional focus on wisdom by Descartes’ accommodation of the new science and cemented into the new paradigm by Kant’s critical move to make philosophy a kind of knowledge, philosophers have been active and full participants in the new approach. There have been suspicions, however, given the ways that certain aspects of modern life seem to have gone astray, that leaving wisdom behind was perhaps, well, unwise. Motivated by this thought, some philosophers want to return to our roots as a discipline focused on wisdom. Philosophers are by strong inclination interested in educating the young, so it is natural for us to want to include our students in this revival. Teaching wisdom in the modern academy, on the other hand, seems a rather difficult task. The notion of the transfer of knowledge, conceived of as collections of facts and their relationships, as the central task of education inclines against teaching wisdom. The methods and attitudes that philosophy has developed while adapting to a world dominated by abundant, scientifically created knowledge, are also impediments. In this paper I will be looking at some of the barriers to teaching wisdom facing a philosopher in modern academia. Broadly, the barriers can be divided into two categories: confusions based on the notion that knowledge is wisdom or at least serves the role that wisdom had previously served, and those arising from the belief that wisdom is a kind of knowledge not too different from the propositional knowledge that other disciplines teach. I will then offer an alternative framework for thinking about the teaching task that focuses on the notion that the goal is not a transfer of knowledge but the beginning of a friendship, a friendship between the student and wisdom.