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Juvenile probationers constitute a population potentially subject to two justice systems but from whom we rarely hear. This study uses life history interviews (see Nelson, 2010) with 30 juvenile probationers who consider self-identified “turning points” that get them into and back out of the justice system. Findings suggest turning points can be either negative (getting into the system) or positive (getting out of the system) in nature. Describing entry into the system, juvenile probationers recount enduring traumatic events and quitting extracurricular activities as negative turning points. When asked to envision turning points that might lead them back out, some report not seeing a way out, while others propose the value of moving out or starting college. Findings suggest theoretical similarities to Sampson and Laub’s (2005) ideas about getting married or joining the military, while providing new options for adolescents. Perhaps more importantly, though, the findings indicate potential discrepancies between the use of probation violations to encourage youth to “wake up” and correct their behavior and probationers’ visions of what might actually help them get on the right track. The presentation concludes with a discussion of the implications of these findings for the system as it tries to create turning points.