This dissertation examines the relationship between a particular method of teaching and learning about careers, and the development of wisdom in young adolescents. By conducting a case study of a specific classroom experience, I examine the ways in which students make meaning of their own career development as well as meaning of the course itself. This study specifically examines Renzulli's Operation Houndstooth theory (2002), which explores six co-cognitive traits Renzulli believes are critical to the development of wisdom. I use three major research strategies: (1) a qualitative analysis of video and written journals and structured interviews, (2) Grounded Theory analysis of the Operation Houndstooth theory and (3) Quantitative analysis of wisdom "scores" and teacher surveys. Data have been collected from video and written journals, structured interviews with students, a structured interview with a Teaching Assistant and a teacher survey. This dissertation supports the idea that teaching about careers using the Enrichment Triad Model leads to the development of wisdom in young people. It also indicates that there may be a missing element in the "Operation Houndstooth" theory: that of the appreciation of connectedness with others. By teaching career development using the Enrichment Triad Model we may be able to promote wisdom in young people, promote social capital and help use careers as a way to rebuild a sense of community and connectedness in American society. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]