In this mixed methods phenomenology rooted in Social Cognitive Theory, a school district in Maryland is examined from an outsider's perspective to determine the degree to which structured post-secondary planning interventions by the district were successful in cultivating career decision resilience in its former students who were in their early post-secondary career training pathways. The information gained is needed because Maryland's recently enacted education law, the Maryland Blueprint for Education, stipulates that school districts make greater investments in students' post-secondary planning rhythms. Recent graduates from the classes of 2018 through 2022 were provided the Career Decision Self-Efficacy Scale: Short Form by Betz and Taylor (2012). A small random sample of those who completed the survey participated in semi-structured interviews with questions aligned to the five domains of career decision self-efficacy measured by the survey. Additionally, the publicly available post-secondary planning interventions promoted by the district were analyzed and compared with the data from the survey and the interviews. The data revealed scores below the norm group in every domain of career decision self-efficacy, but also revealed that participants who developed a meaningful measure of confidence did so through relationship building with school officials, and availability of specialized interventions at the district level for career exploration and engagement. These results align with current understandings of social cognitive theory as it relates to vocational psychology and career-seeking behaviors in developing teens. [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.]