With the processes of migration, globalization and (in our research context: especially) European unification, not only territorial borders but also cultural traditions become fragile (Eberhard et al., 2009). The daily challenges, as well as the opportunities afforded by crossing national, cultural, and linguistic borders, are growing (Beyer & Hopfgartner, 2009; Gellrich, 2009; Homfeldt, Schröer, & Schweppe, 2008). This is true for border regions and especially for those organizations in the border region that explicitly target the issue of border-crossing. We analyze organizations in the Czech-German border-region that are trying to create and to follow a cross-border agenda set in local circumstances and confronted with the difficulties of different national policies. In doing so, two foci are interesting: how the organizations and their members learn to handle the (cultural, political, linguistic, etc.) translational challenges of (existing or attributed) cultural differences, and how the organizations in cooperation with other stakeholders develop a cross-border program of further education.