"The paradoxical theory of change" is the title and theme of a very important and beautiful paper in Gestalt therapy by Abraham Levitsky. There is an approach to strategic family therapy, made famous by the 'Milan School' of Selvini Palazzoli and her colleagues (Selvini Palazzoli, Boscolo, Cecchin, & Prata, 1978), which is based on paradox, and, in fact, their most famous work is entitled Paradox and Counter-Paradox. This chapter reviews the actual Gestalt version of the paradoxical theory of change, and start by pointing out the problems inherent in a naïve reading of the theory. There are some major limitations to a simple interpretation of the paradoxical theory of change in Gestalt therapy. The other assumption behind the theories of self-regulation and paradoxical theory of change is that the client's neurological development can support the self-regulating and growthful responses.