Schools in the 21st century are facing a multitude of complex and multifactored problems (Paisley & McMahon, 2001), including poverty, violence, and poor academic achievement. The intensity of students' needs has led some to question whether school counseling programs are actually comprehensively meeting the needs of all students (Green & Keys, 2001; Whiston, 2002). Ecological (e.g., Bronfenbrenner, 1979) and developmental contextual models (e.g., Lerner, 1995) have been introduced into the school counseling literature as paradigms for understanding and responding to the needs of today's youth (Whiston). These models emphasize the interaction of personal characteristics and the context in which the person lives as central to intervening in developmental contexts such as schools. Models of effective collaboration are needed to best serve the needs of students in 21st-century schools. The Career and Education Connection program, an elementary career intervention developed for an economically challenged urban school district, is described. The article discusses theoretical frameworks and lessons learned through professional and personal experiences with (a) initiating a collaborative research-practice initiative; (b) making connections and enhancing collaborative relationships among university faculty, graduate students, and school professionals; and (c) facilitating graduate student professional development and training.