We analyzed the behavior and psychological changes of those who experienced “preoccupation with habit,” (PH) a state of excessive infatuation with a habit, using the Trajectory Equifinality Model (TEM). Semi-structured interviews were conducted with four research collaborators. By creating a TEM diagram based on the narratives, we proposed a model for self-regulation of PH and examined the relationship between excessive infatuation with a habit and addiction. It was shown that the first step in breaking free from PH was to become aware of the same. Awareness was promoted by others pointing out the PH and by disrupting the daily rhythm of the individual engaging in the PH. However, to become aware of PH, it is necessary not only to receive point-outs but also to be in a psychological state to accept them. Furthermore, it is important to devise ways to distance oneself from the object of preoccupation, and such devising leads to avoiding preoccupation on other occasions and to becoming aware before the degree of PH becomes too high. In the background, it is possible that those who had experienced self-regulation through the device were able to metacognitively control their own behavior.