While navigating educational requirements and career decision making grows in complexity, assumptions about career development and the changing workplace need to be re-evaluated. Quality comprehensive school counseling programs promote self knowledge, exploration, career planning, and self-advocacy skill attainment needed for a time when “good career development requires recognizing that success and fulfillment are individually defined” (Feller, 1996b, p. 152). As a result, school counselors and school counseling programs play key roles “as schools will need to prepare students who can successfully transition to the next level, whether it is a college or university, a community college, a technical institution, or a job. Also, students will need to have the skills and competencies required for the option they choose” (Hughey & Hughey, 1999, p. 207). While changes in work and the workplace require change in career theory and practice (Savickas, 1999), House and Martin (1998) called for school counselors to provide evidence of positive impact on student achievement. Sink (2002) posed questions about school counselor relevancy and suggested the need to ask how to improve school counseling. For those who believe that school counseling, education, and student planning are inseparable, examining long held assumptions about career development deserves attention. This seems timely as Barton (2002) reported that young people are getting no more education than their parents have, and that while college enrollment rates have been increasing, so have noncompletion rates. He also called for more avenues to success than the traditional college route. Appreciating such opportunities, this article provides an overview of the changing workplace and insights about student planning, career and technical education, and school-to-work efforts. Career development assumptions to enhance student, school counselor, and school counseling program success are offered as well.