In recent years, the concept of strengths-based reentry has gained increased attention from scholars and commentators. Proponents of the strengths-based paradigm argue that the formerly incarcerated are far more than a collection of needs and risks. Rather, we bring unique skills to the reentry process that can be utilized to engage in generative activities that serve to diminish the stigma of a criminal history and to promote post-release success. Drawing on my own journey from prison to practicing attorney, this article contemplates the legal profession as one such generative activity. By serving clients at risk of criminal justice system involvement and organizing to promote experiential diversity at law schools and in the bar, many formerly incarcerated attorneys are engaged, often subconsciously, in ongoing stigma/shame management at the micro and macro levels respectively. For these reasons, this paper contends that the legal profession ought to be considered a viable, realistic option for formerly incarcerated students, as they possess the empathy to excel as attorneys and to use the law as a means of transforming their own self concept.