There is a growing awareness that a whole-societal “Great Transformation” of Polanyian scale is needed to bring global developmental trajectories in line with ecological imperatives. The mainstream Sustainable Development discourse, however, insists in upholding the myth of compatibility of current growth-based trajectories with biophysical planetary boundaries. This article explores potentially fertile complementarities among trendy discourses challenging conventional notions of (un)sustainable development – Human Development, Degrowth, and Buen Vivir – and outlines pathways for their realization. Human Development presents relative transformative strengths in political terms, while Degrowth holds keys to unlocking unsustainable material-structural entrenchments of contemporary socio-economic arrangements, and Buen Vivir offers a space of cultural alterity and critique of the Euro-Atlantic cultural constellation. The weaknesses or blind spots (‘Achilles heels’) of each discourse can be compensated through the strengths of the other ones, creating a dialogical virtuous circle that would open pathways towards a global new “Great Transformation”. As one of the main existing platforms for pluralist and strong-sustainability discussions, Ecological Economics is in a privileged position to deliberately foster such strategic discursive dialogue. A pathway towards such dialogue is illuminated through a model identifying and articulating key discursive docking points.