At its simplest, homelessness is a mismatch between income and the cost of housing and can be addressed on both sides of that equation. Demographic data reveals it is important for young people, particularly, to connect to productive career paths in order to avoid ongoing struggles with housing costs and homelessness. This workshop highlights best practices in supporting young people to finish high school, get post-secondary education and training, or get connected to mainstream systems that help them find jobs in their communities.