An organization’s environment has a direct impact on productivity and employee retention, thus affecting the bottom-line. Like classrooms, these “work” environments, both physical and cultural, can effect the success and failure of both the individual and the organization. Exploring the intersection of Progressive Education and the 21st Century workplace, participants will gain insight into what can be learned from Progressive Education to gain the competitive advantage. Google, Amazon, Wikipedia, founders came from progressive classrooms. Work environments that are connected, collaborative, innovative and student/worker centered may enjoy more success and less attrition.