Based on the assumptions of the personalistic-existential concept of the sense of the quality of life, the authors of the article address the issue of planning the outside life by prisoners who were repeatedly sentenced to prison isolation. The article presents the results of a study aimed at comparing the life plans of penitentiary recidivists with their actual implementation, considering it an important determinant of the process of social readaptation and an indicator of prisoner’s efforts to change their current, criminal lifestyle. 245 penitentiary recidivists participated in the study that used the method of the diagnostic survey along with the corresponding technique of a categorized and narrative interview, in a written form. These documents were subject to the content analysis technique, which gave insight into the life plans of the respondents after the end of prison isolation, the discrepancies between the expectations and reality, and their effect on the sense of the quality of life. The results of the study show large discrepancies between expectations of functioning outside of incarceration of the surveyed recidivists and the actual implementation of their life plans. This gives grounds for the statement that this discrepancy significantly reduces the sense of the quality of life of former prisoners, and is a risk factor that may lead to recidivism.