This chapter presents a detailed analysis of four in-depth interviews with four selected teachers. Forty-four interviews were performed for this study, with professors and teachers from all levels of graduate and undergraduate education. It was a difficult task to sort out just four examples that would be most representative for the entire group. Each interview revealed extraordinary personalities, driven in their profession by passion and love toward the act of educating. Nevertheless, to meet the purpose of this chapter, and reflect opinions about both on-ground and online teaching, four teachers were selected. Two of them, Jeremy and Deborah, are practicing only onground teaching. The other two, Derek and Sarah, teach mainly online or hybrid courses, but with experience teaching on-ground courses as well. They were profiled in greater depth in order to allow the reader a better understanding of the teachers’ teaching experiences and their motivation. The names of the participants profiled, as well as the names of their employers or place of employment, are purposely fictitious or vague, in order to protect their anonymity. Many of the issues they bring with regard to teaching in general, or teaching online, mirror issues already reported in prior, existing studies. The background section presents a summary of current findings, with regard to this subject, which are reenforced by the findings of this study. Yet, other issues such as the teachers’ passion for the profession, the delicate interplay among the various facets of online teaching, and the proposed explanation for teachers’ choice of teaching environments are novel to these interviews.