This paper displays the ideological positioning as found in Rudyard Kipling's poem If. It is a poem published in 1910. It presents the embedded ideologies and shows how the poet used the available linguistic resources to achieve his goal. The models of analysis adopted are Critical Stylistics as proposed by Lesley Jeffries (2010) and Stylistic Analysis as submitted by McIntyre (2010). The paper aims at identifying the poet's beliefs to show that success is the outcome of self-control and a real sense of the values of things. It is a try to discover how the poet used various linguistic choices to build a message telling us how to deal with life confidently and identify a line of ideological positioning through Critical Stylistic strategies. The paper presents a theoretical background of the term stylistics and critical stylistics, explaining the adopted models; Analyzing the poem stylistically with a focus on critical stylistic regarding two tools: Representing and Negating for their dominant use in the poem and their effectiveness in interpreting the hidden ideologies. Stylistic devices are used because they steer the text to enable the writer to reach the intended goal. In conclusion, the paper displays that the poet uses the stylistic tools in a brilliant way that leads All, not only his son, to follow and consider it a moral lesson of life.