This article examines four influential programs--Citizen Schools, After School Matters, career academies, and Job Corps--to demonstrate the diversity of approaches to career programming for youth. It compares the specific program models and draws from the evaluation literature to discuss strengths and weaknesses of each. The article highlights three key lessons derived from the models that have implications for career development initiatives more generally: (1) career programming can and should be designed for youth across a broad age range, (2) career programming does not have to come at the expense of academic training or preparation for college, and (3) program effectiveness depends on intentional design and high-quality implementation.