A translation is generally regarded as a transportation of the message from one text into another such that, in prototypical cases, the content of the original or source text is preserved in the target text. Any translation reflects language and cultural contact. It is the effect of a mapping of one language onto another and of one culture onto another. In both cases, it involves a selection of ... [Show full abstract] counterparts. Traditionally, translation is thought of as establishing equivalence between the original text and the translated one. This article explores the notion of equivalence and the closely linked but conflicting principles of fidelity and freedom in translation theory and practice. The issues involved in practical translation stem from a critical selective combination of freedom or fidelity on the part of the translator. Manipulation of either may lead to certain problems. Kipling's poem 'If' is a didactic poem meant to give encouragement. It serves as a motivation as manifest in several traits of a good leader. Maphalla took the initiative to translate Kipling's poem 'If' into Sesotho. This article addresses the idea that the translator's task is not only to convey Kipling's ideas but also to render his style in such a way as to make the translation road smooth to a native speaker of the target language, which in this case is Sesotho. This article also advocates greater freedom for the translator, based on Derridean theory that offers the translator more freedom.