Even though unemployment rates are high among people experiencing homelessness, evidence also suggests that many people in this situation want to work, and, with the right work support and services, they can achieve positive employment outcomes. Many individuals experiencing homelessness are not equipped to secure and retain employment effectively or for long periods of time. Challenges faced by this population consist of outdated or limited job search skills, lack of experience, as well as limited access to tools needed to help improve employability skills. The lack of employment options keeps these individuals in a cycle where they are not able to find stable housing due to a lack of wages and cannot find employment due to a lack of stable housing. Access to a low-barrier employment program is often the only opportunity for a second chance for this population. Breaking down the barriers to employment allows these individuals to rebuild their employment history and develop the skills necessary to gain sustainable employment, make a livable wage, and ultimately secure long-term stable housing.