Some criminal theorists have posited that allowing delinquent teens the ability to work a job decreases delinquent behavior. However, research on the topic remains mixed with some researchers reporting that working a job places extra stress on an adolescent and may encourage further delinquent acts. Criminal theorists have also indicated that one aspect related to curbing criminal behavior, lies in strengthening the ties a potential criminal has with their community. This study seeks to understand how an adolescents perceived outlook on life, relates to their ability to work and handle stress. This study hypothesizes that, the higher a student’s outlook towards the future, the better they will be at coping with stress. Conversely, we believe that the better a student is at coping with stress, the less likely are to struggle with problems related to delinquent school behavior. However, we also predict that the higher a student’s stress level, and subsequent lower outlook towards the future, the more likely they are to have a job, and the more likely they are to report that they have issues related to delinquent behavior in school. Utilizing publicly accessible data, we hope to produce findings that would be of some use to researchers seeking to further explore this topic among adolescent populations currently within juvenile detention facilities. We also hope that this research in some way may be of use to individuals within the criminal justice system as they develop new intervention methods for adolescents within the juvenile justice system.