Most research has studied self-regulation by presenting experimenter-controlled test stimuli and measuring change between baseline and stimulus. In the real world, however, stressors do not flash on and off in a predetermined sequence, and there is no experimenter controlling things. Rather, the real world is continuous and stressful events can occur through self-sustaining interactive chain reactions. Self-regulation is an active process through which we adaptively select which aspects of the social environment we attend to from one moment to the next. Here, we describe this dynamic interactive process by contrasting two mechanisms that underpin it: the “yin” and “yang” of self-regulation. The first mechanism is allostasis, the dynamical principle underlying self-regulation, through which we compensate for change to maintain homeostasis. This involves upregulating in some situations and downregulating in others. The second mechanism is metastasis, the dynamical principle underling dysregulation. Through metastasis, small initial perturbations can become progressively amplified over time. We contrast these processes at the individual level (i.e., examining moment-to-moment change in one child, considered independently) and also at the inter-personal level (i.e., examining change across a dyad, such as a parent–child dyad). Finally, we discuss practical implications of this approach in improving the self-regulation of emotion and cognition, in typical development and psychopathology.