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Much research has been done about deterrence and desistance in serious adolescent offenders. Recent research has begun to address the psychological differences among adolescent offenders, especially in terms of impulsivity, thrill seeking, and risk taking. This paper will examine, within the framework of the pioneering theories of Jack Katz (1988) and Stephen Lyng (2005) on the transformative qualities of certain crimes and the transcendence experienced in edgework, the role of impulsivity, emotional regulation, and psychological development play in the decisions made by serious adolescent offenders about committing crimes. The paper seeks to answer why serious adolescent offenders decide to joyride, stealing cars for the thrill of it, or to jockey, stealing cars to make money, and what factors can be used to predict which serious adolescent offenders will joyride and which will jockey. Using the Pathways to Desistance longitudinal study of approximately 1,354 serious adolescent offenders in Phoenix and Philadelphia, who had been adjudicated of a felony or serious misdemeanor offenses, this research will use data provided in baseline interviews with the 463 of these offenders who reported stealing cars, carjacking, and/or joyriding.