Purpose: We describe a series of more than a dozen studies on self-directed online learning spanning over a decade. Design/Approach/Methods: We incorporated surveys, interviews, focus groups, and content analyses into these research studies, which initially targeted the goals, motivations, and challenges of learners using open educational resources and OpenCourseWare and then focused on learning from massive open online courses (MOOCs). This research accelerated after creating a database of over 3,000 MOOC instructors, through which we explored cultural sensitivity and personalization practices in MOOCs as well as instructional design considerations and challenges, MOOC instructor professional development and career development, instructor motivation and engagement, and student and instructor perceptions of self-directed learning. Findings: This study reveals that self-directed online learners (SDOLs) seek learning environments offering freedom, choice, control, and a sense of autonomy and that both learners and instructors have intrinsic motivation for engaging in open online learning environments. Originality/Value: Based on this research with both MOOC instructors and MOOC learners, we offer instructional design guidelines to address SDOLs' needs and assist in efforts to foster a new generation of SDOLs.