We comment on Aaro Toomela’s article Toomela & Quo Vadis, (Integrative Psychological and Behavioral Science 59:75, (2025), in which the author proposes using Piotr Anokhin’s model of self-regulating system as a general theoretical basis for the development of cultural psychology. In light of self-regulating systems theory living systems, and social objects appear capable of maintaining homeostasis through accommodation in the context of environmental changes thanks to the predictability of environmental changes for the system. As scientific knowledge advances, great ideas formulated in the past reveal their potential for new interpretations and applications. We agree with Toomela about the relevance and potential of Anokhin’s theory for actual development of cultural psychology. However, we assert the necessity along with implying the ideas of self-regulation, to introduce fundamentally different theoretical models, due to the insufficiency of homeostatic models for challenges of the contemporaneity. We argue that the world as a whole, and, first and foremost, humans and human culture, are currently undergoing significant unpredictable changes that go beyond the logics of homeostasis. Comprehending this complex reality requires enhancing the conceptual toolbox of cultural psychology with a different kind of theoretical models — those representing self-developing systems capable of changing their self-regulatory principles over the life course. The idea of this type of development is not new. It echoed in Hegel’s “interruption of gradualness” and in Kierkegaard’s “leap”. It echoes in the works of Vygotsky and Rubinstein. However, to date these ideas have not been operationalized and remain only beacons of future paths for cultural psychology. The difficulties of developing theoretical models of this kind and their relevance to the practical challenges of contemporary development are discussed.