The challenges facing youth who are disconnected from the nation's employment and education systems are expansive. In today's labor market, opportunities for employment at a living wage, and ultimately self-sufficiency, are dismal for those who lack the higher level of skills demanded by employers. The twenty-first century labor market is unforgiving. In the years ahead, over 75 percent of new jobs will require postsecondary education or training. Many employers are increasingly relying on immigrant labor, outsourcing, and outplacement overseas to meet their labor needs. This article provides some insights into strategies that have been implemented to facilitate older youth's transitions to the workforce and highlights the supports youth need for successful adulthood, citizenship, and career pursuits. (Contains 14 notes.)