What makes the design of futures sufficiently transformative? Worldwide, people are aware of the need to change and keep changing to address eco-social challenges and their fall-out in an age of crises and transitions in climate, biodiversity, and health. Calls for climate justice and the development of eco-social sensibilities speak to the need for dynamic and provisional engagements. Such concerns raise age-old issues of inequality and colonialist destruction. Our designs carry the imprint of this current politics, wittingly or unwittingly, into worlds to come. This conversation asked how might we respond fluidly to coming uncertainties, questioning our own practices to sow the seeds of more radical trans-formation, while recognizing the structural forces that can limit or temper opportunities for design activism. It was organized in three quadrant exercises, which we also reflect upon.