In this exploratory study, we track beliefs, preferences, knowledge and information-search strategies of high school students in their final year leading to university enrollment. Namely, labor markets and societies of the modern world are presently troubled by skill- mismatch problems and rising numbers of unemployed and inactive graduates, with significant negative financial and public consequences. While macro indicators seemingly point out a generalized problem, recent analyses pinpointed the issue as being significantly specified by differential under- and over-supply of graduates from specific fields. These results have prompted us to explore the actual decision-making process behind the choice of degree program. We have construed a tailor-made survey to investigate awareness, choice sets, determinants and locus of choice behind this important decision. Our results, while reiterating the complexity of this research object, point out significant difficulties and inconsistencies students and their families face in this pivotal choice. First, ever-growing availability of information is not mirrored by enhanced quality of students’ knowledge neither by the level of their awareness of available curricula. While schooling decisions may depend on individual’s joint expectation of many different events, the data underlying these expectations seems to be scarce and low-quality. Students also manifest significant belief ambiguity regarding their own preferences. Furthermore, in a view of schooling decisions as investments in human capital, future work prospects, while featuring prominently among individual stated choice motivations, are not backed up any sort of thorough and coherent information search strategy, so much so that almost half of the students declare to have never looked up the expected employment and earnings associated with their preferred choice. Finally, we discuss both research and policy implications of our findings. In the case of the former, we identify some novel research questions while for the latter we delineate possible action paths for policymakers, mainly regarding the need for precocious and carefully designed information campaigns and centralized and frictionless databases of reliable university-related information.