American students accustomed to standardization in secondary education have experience with fulfilling the requirements imposed upon them, but often these students require further assistance to facilitate their personal decisions about education after high school. Postsecondary education and career preparation programs, educators, and educational counselors can provide guidance to encourage student self-awareness and goal setting. A literature review was conducted to examine current best practices in educational counseling programs and to determine if self-assessments, including Myers-Briggs and Keirsey personality tests, Visual/Auditory/Kinesthetic (VAK) learning styles assessments, and Holland Hexagon (RIASEC) vocational preference inventories, have been administered to high school students as a component of postsecondary education and career preparation assistance. Available literature suggests that at the high school level, assessments have most often been used as a means to explore dynamics within specified groups. To expand upon the findings available through research literature, interviews were conducted with educational counselors and college/career advisors in both U.S. and U.K. educational settings. From this combined data, a pilot postsecondary education preparation/ career exploration program was developed to address the needs of educators and students in a rural county. The program included SAT/ACT test preparation classes, self-assessment workshops designed to aid subsequent one-on-one educational counseling sessions, and a county-wide college and career planning fair. Three appendixes are included: (1) Interview Questions; (2) Student Assignment Worksheet; and (3) College and Career Fair Data.