Several studies have been performed on the causes and characteristics of juvenile delinquents. However, since there are only a few studies on “recovery” from juvenile delinquency, the definition of recovery from delinquency differs depending on the study, and it is ambiguous on what basis recovery is judged. Therefore, in this study, we used a questionnaire survey to first examine how volunteer probation officers, who provide support to juvenile delinquents in the scene of rehabilitation, perceive recovery from delinquency. The results revealed that many volunteer probation officers considered employment, lifestyle habits, and human relationships to be indispensable in determining recovery (Study 1). Further, although employment is emphasized in support for recovery from delinquency, few studies have empirically demonstrated the relationship between recovery and employment. Therefore, we conducted an interview survey of volunteer probation officers to clarify the process by which juvenile delinquents work and continue employment, and we examined the usefulness of employment in recovery and the issues in employment support. Trajectory Equifinality Model analysis results show that employment alone does not lead to recovery and that recovery occurs through a circular process wherein employment stabilizes when work fosters improvements in lifestyle habits and human relationships (Study 2). Therefore, it is suggested that in support for recovery, both support for employment and support for improving lifestyle habits and human relationships are important.