Thousands of people in this country remain homeless and the unhoused population continues to grow in spite of the increases in the public dollars being spent. Many are losing their chance to leave homelessness behind and become respected, contributing members in their community. The future prospects of those who find themselves without a home, and their capacity for upward mobility are being limited by policy changes at the federal level. This book focuses on how the chance to become self-sustaining citizens, which at one time seemed within reach, is quickly disappearing and preventing those caught in the homeless trap from achieving independence. As these opportunities disappear, so too does the opportunity to interrupt generational poverty. With few avenues available to reduce the size of the existing homeless population and little or no emphasis on slowing the influx of new people becoming homeless, the problems facing many of the largest urban areas in our country have already reached unprecedented size. Drawing from the author's experience as a Pastor, social worker, and director at Volunteers of America operating local homeless programs, this book explores ideas on how we can begin to approach these issues with resources that will once again create opportunities for our unsheltered citizens to leave this cycle of poverty. Creating an exit plan for many of our homeless can ultimately create a humane approach to turning the corner on what is becoming the most pressing social issue in our nation.