This study investigates translation choices and challenges in the translation of two training guides focused on running. It tests the validity of Reiss’s text-type theory in the translation of cultural aspects. Furthermore, the study discusses to what extent equivalence can be reached when translating an aesthetic language and finally, it comments on some characteristics of typical runners’ language. The results show that Reiss’s text type theory is not sufficient to guide the translation of cultural differences in the SL and TL but an analysis on phrasal and lexical level is also needed, where Koller’s equivalence relations and Newmark’s communicative translation are applicable. The results also show that figurative language is indeed possible to translate in these kinds of texts, where among others compensation proves a useful strategy. Equivalence on all levels of the text, however, is not always possible to reach. Finally, the findings of a special runners’ language were rather limited, although some examples indicating a presence of a runners’ jargon were found.