Students learn best when teachers get out of the way. Unfortunately, university classrooms continue to be intensely teacher-centric, are driven by the teacher's agenda and calendar, and embrace simple models rather than complex alternatives. These simple types of learning environments frustrate students' development of the risk-­taking and choice making confidence they need in the workplace. Bain (2004) makes the point that environments embracing choice as a priority, welcoming risk-taking, and nurturing students who make mistakes, better prepare students for professional success. In this article, we intend to provide context to the conversation about how learning-­risks and agency impact and promote the individual growth of the student when the teacher gets out of the way. Using a Rapid Assessment Process (RAP) (Beebe, 2001) combined with Action Research (AR) (McNiff, 1988; Stringer, 2007; Schön, 1983; Argyris, 1993) we devised an experiment to determine if a university course would invite more student growth when the environment changed from being teacher-­centric with highly structured assignments and critical assessments, to one that embraces the tenets of complexity theory. The purpose of this approach was an attempt to challenge the status quo; to show how complex interactions between risk-­taking, agency, learning culture, teacher-facilitator-­mentors, peers, coursework, and outcomes are important to students' preparation for successful professional work. To accomplish this we experimented within a software development course at a large university in the northwestern United States. We found students appeared to be more prepared to move on to the professional workplace and demonstrated professional ways of being when they had experienced risk-taking and agency in a learning environment based on complexity theory principles. Without many examples of complex research or course design processes to follow, we envisioned and applied processes for both.