Journal article by DR Perpetua Kalimasi & Nsikwa Chisalala submitted at Uongozi Journal of Management and Development Dynamics Vol. 27(1) (2016) 34- 84This paper aims to explore student’s pathways to post-secondary education in terms of trustworthiness of relevant information about university education, working life and respective successful transitions. It is anchored on the boundary crossing conceptual framework to explain the gap existing between secondary school, college and working life choices. Using a case study design, a list of questions collected during 2016 TCU exhibition at Mzumbe pavilion has been analysed and reveals a range of information gap amongst prospective university applicants. In addition, by reviewing relevant literature on students’ transition, analyzing relevant documents, this paper offers an understanding of initiatives used by various stakeholders to prepare students for higher education and working life and associated challenges. The review of literature and documents reveal that there are no clear coordinated strategies across stakeholders with regard to preparing students for post-secondary education and career progression on the one hand and there are insufficient welfare upport services to students to promote the needed information on the other. Based on the challenges and conclusion, some recommendations have been proposed as a basis for best practices to address the post-secondary transition paradox.