With the goal of examining sustainability through a new lens this research project explores the link between inner transformation and sustainable action, with particular emphasis on how leaders of small enterprises (SE) are reconciling their role in the world today and into the future — and what it will take to realize that future. While hardly exhaustive, this report argues that the transition to sustainability depends on two rather ambitious fronts: i) To reframe the problem to include a shift in mindset toward postconventional or systems-consciousness at the individual level and, ii) To reimagine the critical role of SEs in shifting business practices toward a desired sustainable state at the organizational level. This research project therefore draws on in-depth interviews with eleven SE leaders of sustainability-driven models of organization to discern the difference between the inside causes for a shift in SE leader mindset - a significant finding to accelerating the transition to sustainability - and the outside effects of a shift in SE leader mindset toward a more sustainable enterprise.