This empirical paper addresses the need for more in depth understanding of signs and characteristics of transgressive learning in a context of runaway climate change. In a world characterized by systemic global dysfunction, there is an urgency to foster rapid systemic change which can steer our paths towards meeting the SDG goals. The contention of this paper is that, although there is a need for rapid change, it is fundamental to understand how such change can come about, so as to co-create and investigate learning environments and forms of learning that can lead to a systemic change towards sustainability. Anchored in the emerging concept of transgressive learning, this article employs the innovative Living Spiral model to track critical learning moments by facilitators and participants in multi-stakeholder Transformation Labs (T-Labs), which took place in 2017/2018 in various grassroots sustainability initiatives in Colombia and The Netherlands. The results of the analysis highlight the importance of the values of “acknowledging uncertainty”, “community”, and “relationality” in disrupting world-views through promoting reflexivity in participants and facilitators. This paper concludes that more research on the power dynamics of “absences” in transformative research is needed to better capture the challenges of overcoming sustainability challenges.