Young adult men (ages 18-24) who exit the juvenile justice system are at high risk for repeat offending. However, little is known qualitatively about the strategies that they use to navigate criminal influences, crime temptations, and the possibility of getting "caught." To address this gap, the authors used narrative methods involving 30 in-depth qualitative interviews with 15 formerly incarcerated young men between the ages of 19 and 24. Coding and memoing were used to identify major themes and data patterns. Results indicated two distinct groups; one group engaged in a series of micro-level decision-making processes to navigate challenges in their everyday living environments, which helped to facilitate their gradual abstinence from crime. The second group was equally tested by contextual challenges, but they made decisions to minimize their criminal involvement to avoid the risk of repeat incarceration, which negatively influenced their desistance patterns. The results lend themselves to better understanding how decision making, internal motivation, and external factors can influence the desistance processes of transition-age urban young men.