When Bill Gates published his book “The Road Ahead” (1995), he summarized the transformative implications of the personal computing revolution and described a future profoundly changed by the arrival of a global information super highway. Almost twenty years later, the tsunami of online programs and the MOOCs (massive online open courses) is impacting the structural integrity of post-secondary institutions and changing the competitive landscape of higher learning at an unprecedented pace. When Allen and Seaman (2013) asked the question of whether faculty acceptance of online education increased in their Sloan Consortium annual report, only 30.2% of chief academic officers believe their faculty accept the value and legitimacy of online education. This rate is even lower than the rate recorded in 2004. With an apparent widening gap between institutional strategy and faculty acceptance, each organization needs to conceptually map its road ahead. However, only an institution as a whole can decide for itself what kind of change is needed and define what constitutes evidence of lasting change. This implies a unique transformation of institutional philosophy, culture, strategy, and reward systems for faculty members. Complex adoptive system (CAS) theory (Olson & Eoyang, 2001), suggests that the most powerful organizational transformations occur not at the macro level but rather at the micro level where behaviors and changes began to emerge. Thus, instead of trying to measure, evaluate, or categorize which faculty member fits into which stage of online faculty development under which framework, this study asked four tenured faculty members to reconstruct their experiences on why they teach online, how they learn to teach online, and what factors influences their journeys to teaching online. Their narratives painted a landscape of faculty acceptance in institutions and the online learning phenomena in our society. Ultimately, their stories are really about change. By studying the “change agents” in a changing organization in a changing industry, this study is not an exercise to identify the best practices. Rather, this study hopes to inspire new ideas for new ways to conceptually frame the problem facing the faculty, the institution, and the industry in their road ahead in teaching online. The researcher hopes that this study may be used by institution leaders, faculty developers, and other faculty members to: (1) assess the level of progress of their current and future distance learning program, (2) determine how distance learning programs should be established, (3) evaluate faculty development efforts, (4) improve strategies and implementations for institutionalization of their distance education programs, including academic programming and faculty reward structure, and (5) improve online student retention and learning outcomes.