The purpose of this research was to explore the gaps in college and career readiness (CCR) skills for secondary students and the possible solutions for filling readiness gaps. This qualitative case study interviewed students, teachers, college professors, and business leaders to determine the gaps in the skills of new college students and employees and to understand each participant's experience surrounding CCR. A constructivist grounded theory approach to data collection and analysis was utilized to highlight the diverse nature of each participant's experience and the researcher's role in the analysis process. Through the analysis of the interviews, the study uncovered four thematic takeaways regarding CCR: 1) businesses and colleges identified soft skills as focus areas for first-year students and new hires, 2) curriculum structures and methods at the high school level do not provide the supports necessary for soft skill development, 3) more supportive programs are needed at the secondary level to introduce students to college and career information, and 4) challenges from the COVID-19 pandemic have contributed to the lack of certain soft skills in students and new hires, consequently increasing demands for flexibility and accountability in the workforce. Recommendations and models of CCR support programs to meet the gaps in readiness are discussed, as well as possible areas 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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]