Abstract: On April 4, 2001 (i.e., “441”), Charles Vest, then president of MIT, made an historic announcement. He set a goal of having most of his university’s courses freely available on the Web in a decade. While some thought this to be a rather bold proclamation, today more than 2,000 MIT courses are available for self-directed learners around the globe to explore, download, use, and share. Suffice to say, we are in the midst of an incredible array of changes across all sectors of education that would have been unthinkable just a decade or two ago. People in remote parts of the world are learning from well-known professors at Princeton, Rice, Harvard, and MIT; typically, without a fee. Countless millions of individuals are engaged in self-directed, informal, and solitary learning experiences with open educational resources (OER) and OpenCourseWare (OCW). At the same time, myriad others are engaged in highly collaborative and interactive learning with global peers who have signed up for a MOOC or “massive open online course.” As these learning experiments unfold, many aspects of college, and schooling in general, are being called into question. There is debate about the value or even the need for a degree. In response, this study explores the learning experiences of self-directed learners, including the common barriers, obstacles, motivations, and successes in such environments. It also explores possibilities for life change from the use of OER, OCW, and MOOCs. Data collection included subscribers of the MIT OCW initiative as well as participants of a MOOC hosted by Blackboard using CourseSites. The findings not only capture the motivational variables involved in informal and self-directed learning experiences through informal education channels, but also provide a set of stories of life change that might inspire others into MOOCs, open education, and beyond.