This article presents a speech delivered by the author for the Kent M. Christiansen Memorial Lecture series in April 2008 at Arizona State University. The author discusses why he thinks that approaches to academic advising theory and research that arises out of the humanities can be of great value to practitioners in the field of academic advising. The author believes that academic advisors can learn a great deal about advising if they approach it in the same ways that other academics approach their subjects in literature, philosophy, and history. Moreover, he claims that academic advisors can use the same kinds of tools that they use to do their research: (1) imagination; and (2) interpretation. The author also focuses on the role of theory and research in academic advising.