This paper draws from qualitative interviews with Chicago-based formerly incarcerated individuals (FIIs) who work in criminal legal system-related fields (e.g., law, reentry, policy advocacy, education, etc.) to examine the unique human and social capital FIIs bring to their roles. Previous literature largely centers around employment barriers faced by FIIs, the effectiveness of violence prevention organizations, and peer work, with few studies exploring the relationship between incarceration and qualities relevant to criminal legal system-related work. This study finds that FIIs in these fields possess knowledge, technical/soft skills, resilience, connections, credibility, and relatability derived from their lived experience. It also finds that they face an array of work-related barriers and challenges such as limited facility access; parole, probation, and supervision restrictions; difficulty striking a work-life balance; re-traumatization; and tokenization, exploitation, and under-compensation. The paper concludes by recommending barriers be removed and opportunities be expanded to help FIIs further engage in this work.