To develop the cognitive, social, and career skills needed to succeed in the modern workplace, students must learn to think creatively, apply their skills innovatively, and take risks constructively. Implicit in this position is the expectation that students will have the self-confidence to apply their knowledge in both familiar and new settings and feel connected to the world at large to share what they know with others. The authors are working to accomplish these goals through Year Up, an organization that is designed to help young adults bridge secondary to postsecondary opportunities. Personalizing students' learning experiences is central to Year Up's philosophy that success depends on creating an environment in which students feel safe enough to learn from their mistakes; where instructors provide honest, nonthreatening feedback; and where all students are able to demonstrate their mastery of knowledge and skills in ways that are personally meaningful. By applying this philosophy consistently, caring adults can have a lasting influence on the trajectory of a young adult's life. Although Year Up is designed as a yearlong program for 18- to 24-year-old students who have already graduated, the lessons learned over the course of running this program have implications for secondary school leaders. The lessons reinforce the importance of advisers, mentors, and learning communities to support student growth and professional capacity. (Contains 1 figure.)