This paper is a qualitative case study analysis of the development of a fully online learning community of graduate students through arts-based community building activities. With increasing numbers and types of online learning spaces, it is incumbent upon educators to continue to push the edge of what best practices look like in digital learning environments. In digital learning spaces, instructors can no longer be seen as purveyors of content knowledge to be examined at the end of a set course by a final test or exam. The rapid and fluid dissemination of information via Web 3.0 demands that we reshape our approach to teaching and learning, from one that is content-focused to one that is process-driven. Rather than having instructors as formal leaders, today’s digital learning environments require us to share expertise, as it is the collective experiences and knowledge of all students together with the instructors that help to create a very different kind of learning community. This paper focuses on innovations pursued in a 36 hour 12 week graduate course in higher education entitled “Critical and Reflective Practice”. The authors chronicle their journey to developing a fully online learning community (FOLC) by emphasizing the elements of social, cognitive, emotional and digital spaces that form a moving interplay through the community. In this way, students embrace anywhere anytime learning and often take the learning, as well as the relationships they build and skills they acquire, beyond the digital class into real world situations. We argue that in order to increase student online engagement, pedagogical approaches need to stem from two primary elements, both creativity and critical reflection, that are essential pillars upon which instructors can co-design learning environments with students. The theoretical framework for the paper is based on the interaction and interdependence of Creativity, Intuition, Critical Reflection, Social Constructivism and FOLCs. By leveraging students’ embedded familiarity with a wide variety of technologies, this case study of a graduate level course on critical reflection in education, examines how relationships, quality of work produced, and student engagement can improve by using creative and imaginative pedagogical strategies. The authors examine their professional pedagogical strategies through the lens that the teacher acts as facilitator, guide and co-designer. In a world where students can easily search for and organize information as self-directed processes, creativity and connection can at times be lost in the digitized course environment. The paper concludes by posing further questions as to how institutions of higher education may be challenged to restructure their credit granting courses into more flexible modules, and how students need to be considered an important part of assessment and evaluation strategies. By introducing creativity and critical reflection as central features of the digital learning spaces, notions of best practices in digital teaching and learning emerge.