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From June through August 2012, I lived in a halfway house doing participant-observation and interviewing former prisoners. I did basic training to prepare a resident to work as an interviewer in the project, and together, we completed 25 life history interviews, half each. In 2013, I returned to the house for another three months, and re-interviewed half the people from the original network. The difficulties of going straight have been palpable throughout the project: everyone interviewed has been imprisoned multiple times - the average is four sentences of more than 60 days. But in this paper, I focus on the “success stories,” examining the policy implications of the experiences of those who effectively established new lives on the outside. This tended to involve an internal shift, with individuals growing determined to change, as well as an external, institutional opportunity to put this into practice. Community colleges – with their nonjudgmental educational atmosphere - and social service employers – with their rewards for native knowledge – were especially important for many. I argue their experiences support a strategy of creative decarceration, not only promoting policies that reduce prison populations, but building institutional spaces of healing that support people to make good choices.