In the early summer of 2009 David Dietrich was a tenured faculty member at Lambuth University, a small liberal arts college when a friend from the University of Tennessee (UTM) at Martin called about a job opportunity. Because Lambuth had been struggling financially for many years and there was talk of the school closing its doors, Dietrich was interested to know what this new position was all about. Knowing only that the opportunity at UTM involved a position in their counseling masters program, he was surprised to learn that this program was entirely online. The program had adopted the online format in 2007. Dietrich was being asked to come to UTM for a year, with the chance to be hired tenure-track after that year. The practical decision was an easy one. He needed stable work (Lambuth closed in 2010). But once he joined the program he was forced to seriously evaluate his thoughts about online education in general, and the online education of counseling students specifically. This article outlines some of his initial thoughts, the changes in thinking that he has had since he began online teaching, as well as a description of his process of learning how to teach online.