It was spring of 2004 when Joe Cytrynbaum interviewed to become the Program Director at Umoja Student Development Corporation in Chicago. Umoja is a weird hybrid of a youth development/educational reform organization. The organization operates from the premise that all sustainable change (for individuals and systems) has to happen in the context of meaningful relationships; that purposeful relationships are the first step in making anything better--even the hard core, long-term impacts of poverty. Its operational formula is part art and part science. It involves moving into the most under-resourced and under-performing high schools in Chicago and walking beside students in their journey. In this article, the author offers a remarkable glimpse of Joe at work at Umoja, the Chicago youth advocacy organization Joe joined immediately after his graduation from Penn's doctoral program in education, culture, and society.