The paper is an attempt to show Virginia Woolf's 'struggle' to make 'ordinary' (life, being and language) become 'extraordinary'. 'Orlando. A Biography', a text begun sometime in early October (8th) 1927 'as a joke' and finished on the 17th of March, 'as the clock struck one' (AWD:160-161), 1928, may be considered as the prematurely born child of a mind endowed with 'one rare gift': that of seeking. It is the seeking of the 'Word' which constitutes the backbone of this 'joke'. And yet, behind laughter and light-heartedness, there is a serious desire to discover 'the most necessary thing to me (Woolf)' (AWD:169): the 'reality' of the creative self through time. Thus, the Orlando-biography invites the reader to decode it as an autobiography, which, finally, proves to be a recording of a spiritual journey to attain freedom, stylistically achieved through a game of positings and modes of reading and writing. In order to show the process of shaping the creative self in 'Orlando', we have used some strategies offered by approaches such as: a. phenomenological (offering insights into moods, states of consciousness and the methods used 'to investigate' 'second selves' (AWD, l925) -'.... opened and intensified as it ( the mind) is by the heat of creation' and 'to expose' one's mind, body and self 'to the blasts of the outer world' (op.cit., l935); b. pragmatic (helping the reader to see how ' ... the words' can be made 'to glue together, fuse and glow' (AWD, l924 ) and how 'sentences form and curve under my fingers' (op.cit., l935) in order to 'convey the true reality' (op.cit., l923) to somebody; c. and semiotic (unfolding Woolf's game of minimalising or expanding some meanings, in and through time, which makes out of the word in Woolf's text a dynamic sign). The three approaches will help the reader to see the Woolfian text as a sign-within-a-sign-within-a-sign. The 'Orlando-joke' finally proves to be a complex game of positing the (creative) self in a temporal abyme, hauteur and surface (Cmeciu 1999), which is unfolded through a metaphoric and metonymic mode (Lodge 1989).