Intentional communities are particularly relevant in their pioneering path towards innovative sustainable lifestyles, often following an integrative approach of sustainable development. From a socio-cultural perspective their innovative methods nurture intra-personal growth processes based on a matured conflict culture and a peaceful coexistence culture in regards to both human and natural systems. This chapter aims to address the influence of personal sustainability on transition pathways in conceptual, methodological and empirical terms. It explores how three selected community-design practices foster personal sustainability competences of community members, especially for inner conflict resolution and self-empowerment. Furthermore, the community-led approach to personal sustainability is explored regarding its actual and potential interactions with wide-scale systems transformation. This perspective seeks to broaden the established notion of sustainable development by including ‘alternative developments’ and ‘alternatives to development’. Regarding this, the argumentation refers to ‘alternative sustainable development’ approaches proposed from and lived by members of the Global Ecovillage Network (GEN), where personal sustainability - embedded in the everyday life of communities - can be understood as a lifelong learning process.