A person's sense of belonging with society has been described as being a convergence of cognitions, behaviours, and emotional affect as well as an environmental experience (Pretty et al., 2003). Moreover, the desire for a sense of place belonging within society is not constricted by age, gender, ethnicity, or economic status. For as Antonsich (2010) points out, both society's 'insiders' and 'outsiders' have an inherent longing to claim bodily, temporal and/or ephemeral ownership of society. Once they have located this space, their sense of belonging is realised through their physical or cognitive occupation of that space... In doing so, they generate a within group sense of identity which further contributes to their sense of place (Taylor & Khan, 2014). This chapter examines the psychological motivations of graffiti writers for initially selecting a societal 'outsider' (but graffiti subculture 'insider') graffer social identity within the broader context of the psychological conceptualizations of people's sense of belonging, subcultural sense of place, sense of community and sense of connection. This chapter concludes by highlighting the motivations behind sanctioned graffiti artists drive for social inclusion (i.e., transitioning from a societal outsider to a societal insider).