This chapter maps the wandering, the journey and walk through a city where the cultural identities provide a sense of uncanny for the a/r/tographer himself in his becoming creative writer. As a person growing up between Chinese and Javanese values, the experience of living and studying in Macao for five years provides the unheimlich setting where some of his cultural values are (re)experienced and (re)contextualized differently. Within this setting, the a/r/tographer as an assemblage of identities walks through another assemblage – the city with yet multiplicities of identities. The familiar, the uncanny, and the strange are engaged in seemingly randomencounters, creating spaces for dialogue, interrogation, and art-making. It is through these encounters that the inquiry of home and identities is engaged and acted upon the process of becoming creative writers and walking pedagogy of self. The resulting poems are often multilingual, illustrating dialogues between different identities and other multiplicities within the assemblages.