This paper describes my journey from instructional technology professional and doctoral student to instructional technology leader and tenure-track faculty member. I reflect on 15 years of application, in government, industry, and higher education, of what I learned in the classroom from some of the giants of the field (Wager, Morgan, Kaufman, Dick, Keller, Harless, Reiser, Driscoll). With the continuing proliferation of technology throughout all levels of higher education, systems thinking and the instructional systems design (ISD) process is highly relevant and germane. Its application, however, must be done with care as many people do not understand it and it is applied within a complex, imperfect social and organizational cultural context that requires compromise, consensus building, patience, and a willingness to proceed slowly. The growing role of technology in organizations, and especially e-Learning in education, has increased the need for systems thinking and systemic change in order to manage rapid change.