The research explores how undergraduate students in Bangladesh choose between pursuing corporate careers and starting their own businesses. Drawing responses from 350 students enrolled at 13 different public and private universities, the study applies both survey-based data collection and statistical learning methods to identify key decision-making drivers. Factors such as financial considerations, job security, societal norms, internship exposure, and lifestyle expectations were critically examined. The analysis revealed a noticeable shift in student interest toward entrepreneurial paths, particularly among those valuing independence and adaptability, though a strong inclination toward corporate positions remains due to perceived financial and professional security. Using Chi-square evaluation and various classification models, the study found that personal mindset, family background, and practical experience were highly influential. The outcomes highlight the need for universities to provide targeted support, such as mentorship and entrepreneurship education, to better prepare students for varied and changing career landscapes. These insights can inform academic planning and policy development aimed at nurturing career readiness in higher education.