The purpose of this qualitative study was to investigate the influences of prior work experience in the classroom of career change secondary business educators. The 21st century workforce is rapidly evolving due to increases in innovative technology and global competition. Educators are expected to prepare a digital generation of students to face the challenges that lie ahead as they transition into this new workforce. To meet the needs of this new generation, teachers are increasingly being expected to teach 21st century skills that include technology literacy, collaboration, and communication. High attrition rates and an increasing teacher demand continue to be critical issues facing education, and career change educators may play an important role. Business education encompasses many of the 21st century skills, and a career change business educator has first-hand knowledge of the 21st century workplace. The research questions focused on the influence of prior work experience as it relates to business education curriculum, instructional strategies, and expectations of teaching. The collective case study included interviewing five career change business educators and five principals who observed their classes. Observations were conducted in the career change business educators' classrooms using a rubric based on the theoretical framework of Dewey's Pedagogies of Engagement. Common themes emerged through within-case, cross-case, and constant comparative analysis. Themes included possessing unique personal characteristics and perspective, having a passion for business, making learning relevant, bringing content to life through personal stories and experience, and extending curriculum to teach life lessons and character traits. These educators engage students in teamwork, collaboration and problem solving within the classroom and the community. They use technology creatively and innovatively to engage 21st century students, are seen as technology experts, and are often asked to develop and deliver formal and informal training. Regarding expectations, themes included feelings of isolation, little need for support, little flexibility, and satisfaction in the career change. These educators stay connected to the workplace, pursue continuing education, and keep up with the challenges of technology. Recommendations were included for school districts, for teacher preparation programs, for those considering a career change into teaching business education, and for further research. [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.]