Scholarship is revealing increased evidence of the successful accomplishments of e-learning practitioners. Yet, there is no shortage of research underlining the presence of those who fail to recognize the potential of technology applied to learning contexts, the so-called ‘resisters’ to e-learning uptake, especially in higher education blended programs. Less is known about how to inspire individuals, especially if they hold key positions in these contexts, to move from one side of the line to the other. This paper reports on such a case. The report records the experiences of a seasoned educator and director, with both feet firmly embedded in traditional 20th century teaching practices, who, with guided e-learning advice and support over a 5-month academic semester, becomes a ‘convert’ to 21st century social learning practices and an active promoter of the social media tools that support these practices. The inquiry is focused on the changes to practice and mindsets in learning of both the educator/director and learners that took part and benefitted in this trajectory. Qualitative data sources were individual interviews, field and reflective notes and observations as well as evidence from analyzing social media content. Whereas some scholars would have us believe that it is solely by compiling positive evidence of the benefits of e-learning that we will reach universal acceptance and adoption, this inquiry clearly indicates that the journey is much more complex. As many of us concerned with promoting sustained quality development in education realize, particularly those involved in parts of the world where this development is most elusive, the study results reveal that it will take more than positive marketing to make lasting conversions to e-learning happen. We believe that the model that leads the way to such a goal is based in current learning theories – a sociocultural-based, constructivist process that requires an investment in time and the support of stakeholders at all levels.