Understanding and accepting the important roles of failure and mistakes are keys to developing a successful online pedagogy. Students arrive with a wide variety of backgrounds, not only in the course content but also in technological skills. Thus, the development of confidence in the value of our mistakes, and the expectation to make mistakes are important. As Schon reveals, we feel like failures “whenever learning a new competence requires unlearning deep-seated theories-in-use or whenever in situations of uncertainty feelings of vulnerability and ‘knowing what to do’” evoke a failure response” (1987, p. 290). It is important to cultivate our errors as sources of important information and pivotal learning moments. As athletes and other high performers do, analyzing our errors can be an important touchstone from which we can move forward. If students “hold unrealistically high expectations for their performance, once they become aware of their error, they believe they should produce complete and perfect interventions. They see error as failures and a blow to self-esteem” (Schon, 1987, p. 291). Learning from mistakes is a pattern followed by the best performers across professions. As sport psychologist Terry Orlick attests, failure can be instructive more quickly and accurately than any other learning experience (2000). Here again, using digital moments creates a safe and supportive learning community within which risk-taking is encouraged resulting in significant personal growth and innovative thinking in students