This chapter explores possible tradeoffs teachers identify in relation to online teaching. Instructors, in the process of teaching, have to constantly interact with their students, with their peers, with academic departments, with school administrators, course developers, and many others. The environment in which they function—the form of teaching—poses specific challenges they need to recognize and manage in order to maintain their effectiveness as teachers. The subjects who were interviewed for this book share their perceptions and experiences regarding the potential and actual tradeoffs to online teaching. They try to compensate, for example, for the lack of visual communication cues factual in the online environment, by modifying the design of the presentation slides they use in class and by changing the format of the course to adapt the materials to the different modality. They also note behavioral changes and gains in communication, with some teachers reporting changing to a completely different online persona. The tradeoffs lead to adjustments that may affect the instructors’ communication style, teaching style, and even their entire teaching philosophy. Ultimately, these affect their career choices.