In Chapter 7 the authors explore the difficulties legal prostitutes experience transitioning out of sex work. Employers often seek universal or “transferrable” skills when hiring, and are less concerned about industry or occupational experience, as long as core skills are visible on applicants’ resumes. However, legal sex workers, like other people in stigmatized occupations or industries, must often hide their work history, which creates challenges for advertising their transferrable skills. This presents a problem of mobility. In this chapter, we argue that employers’ reliance on work history transparency and their desire for transferrable skills creates a paradox for workers in stigmatized fields. These workers must disclose their work history to reveal their transferrable skills. At the same time, they often cannot disclose their work history and the valuable skills gained in their stigmatized occupations. This prevents the transfer of skills, and ultimately, mobility out of stigmatized occupations.