The aim of the present paper is to share the outcome of a series of professional conversations among three scientist practitioners on how the new concept of transition environment (TE) and two related models may inform a sport psychology practitioner’s (SPP) work with football players in their cultural transitions to foreign football clubs. The center of the discussion was the applied work of one of the authors who is in a position to help Danish professional footballers with transitions abroad. After outlining his professional philosophy, developed for working within the context of professional football, we explore the tasks and challenges for practitioners working with footballers in a cultural transition. We explain how the context of professional football constrains the services. Ideally, the SPP would like to optimize the players’ environments during transition but ends up using specific strategies to compensate for a lack of access to this level of work. Finally, we promote the importance of SPPs possessing contextual intelligence in order to help players understand and navigate their TE.