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The entrepreneurial mindset is increasingly crucial for K-12 students, yet few studies have explored whether traditional assessment systems can measure these non-cognitive skills or if traditional schooling can foster their development. This quantitative observational study, using data from 209 students, explored the relationship between entrepreneurial mindset and college and career readiness skills, and how these relationships vary across demographic groups. Findings showed a significant but weak correlation between entrepreneurial mindset and readiness skills, with notable variations by demographic characteristics in the relationships and readiness skills. The study highlights the limitations of traditional assessments in capturing non-cognitive skills, advocates for specialized programs for entrepreneurial mindset, and calls for further research on how social backgrounds impact educational outcomes and assessment systems.