Technical Vocational Education and Training (TVET) has fundamentally been the avenue for creating technically skilled graduates whose skills were meant to have been fused into Ghana’s industrial sector to improve and ensure performance at the highest level. For this reason, technical universities have been established in each of the ten (10) regions to provide targeted skilled education to students. Unfortunately, certain challenges have hindered the ability of these technical universities to live up to its core function in Ghana by preparing students to take up entrepreneurship activities. The crust of the study was to identify the transitional challenges and suggest actionable strategies that can be adopted to improve the fortunes of technical universities towards creating a more sustainable educational system that can make School-work transition easier for graduates. The study objectives covered from identifying the transitional challenges, strategies that can be adopted to remedy these challenges and the benefits of TVET as a strategic means of reducing the rate of graduate unemployment. The study adopted a mixed method research design and used both qualitative and quantitative methods to collected primary data using questionnaires and interviews. Even though other challenges were identified, the findings revealed the most peculiar challenge is lack of supportive system during transition and the disconnection between curriculum and business needs. The study therefore recommends government to formulate policies for the smooth transition of these graduates, employ professionals and develop work-based courses to enhance the attractiveness of Technical universities.