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Employment has consistently been cited as one of the most effective protections against recidivism for formerly incarcerated people; however, in addition to other barriers to reentry, job-seekers with criminal backgrounds face additional obstacles when searching for work. Prison time weakens social ties important to securing employment, creates gaps in employment history, and erodes vital job skills; these issues, combined with the stigma of possessing a criminal record, dramatically reduce formerly incarcerated job seekers’ chances of securing post-prison employment. Even when all other barriers to employment are overcome, former felons are required to report their criminal records on employment applications, at which point, the stigma of past criminal convictions often prevents “ex-cons” from being hired. This paper serves as a qualitative intervention in the existing literature on job-seeking after prison and an expansion of our scholarly understanding about the decision to desist from crime. Through in-depth, qualitative interviews with excarcerated job-seekers, this paper addresses the lived experiences of applying for work after prison, the ethical dilemmas faced (to be honest and report one’s convictions or to lie?), and how these dilemmas influence formerly incarcerated job-seekers’ decisions to pursue legitimate work or, instead, to sustain themselves via extralegal means.