This paper will concentrate on the current shift from teaching to entitlement learning that has become a significant part of our educational discourse and culture. With increasing emphasis on accountability and high test score, students have become active recipients in "assessing" and "evaluating" the effectiveness of their learning experiences. Increasingly, students appear to equate their academic expectations as "educational purchases" in which their financial investments in higher learning should earn them profitable margins (opportunities) or estimated returns (high grades) by the end of their academic journey. This shift in thinking has created a "Pedagogy of the Obsessed".