This study investigates how personality and individual experiences influence decision-making processes during the transition into Higher Education (HE). It offers insights into application choices, where applicants employ different quantitative hedging strategies against non-admission. These strategies are assessed by the number of applications but also the search radius, leading to an alternative's inclusion into the application set. An empirical analysis of the usually unobserved application stage shows how these hedging strategies depend on applicants' perceptions of psychic costs and their socio-demographic backgrounds. This heterogeneity may explain varying participation rates for different subpopulations in a country with a large HE sector, such as Germany. An essential finding points to the relevance of earlier mobility experiences during adolescence, which may act as facilitators of subsequent student mobility. Providing adolescents with a stimulating mobility experience before they consider transitioning to university could thus be an avenue to increase participation chances of potentially disadvantaged groups.