One of the most important functions of learning is the formation of identity. From a hermeneutical viewpoint the formation of ipse-identity is, to a large extent, based on the meaning of the learning experiences. The following questions guide our research: first, what meanings do Estonian and Finnish students gain from curricular facts? And second, what do students in the two countries consider important to learn for their future? The theoretical framework of the study is based on ontological and socio-cultural approaches to learning. Both traditions recognize a connection between one's personal agency as well as structural factors concerning learning contexts. It was found that in meaningful learning contents youth, on one hand, gain authentication of identity, while on the other, they feel the pressure of insecurity and coping with the idea of an uncertain future.