This paper presents design based research on the role of self-direction in online learning by exploring elements of both individual and collective engagement as significant aspects of learning. By making the claim that online instruction draws on autonomous and social aspects of learning, this paper examines how online teaching environments are informed through an orientation of social constructivism in learning that requires educators and learners to recognize the value of inquiry and higher order of learning through individual reflection and collaborative discussion. Recognizing specific challenges for educators and learners through the combination of high learner expectation and autonomy, this discussion proposes how a focus on individual control and group responsibility can address complexities in online learning through an action learning approach to education.