Recently, rappers Talib Kweli and Evidence discussed the conflict between rapper-identity and individual-identity as a person ages, with Kweli describing how a rapper’s persona ‘becomes like an armour’ and Evidence observing that ‘after a while that stops getting rewarding’. (People’s Party with Talib Kweli 2019: 6:54). These observations highlight the difficulties for artists to be able to express their own growth and development as their artist personas become ‘fixed’. This fixing or flattening of persona, combined with a hypermasculine culture (that reflects a society) where even the phrase ‘to catch feelings’ is a derogatory term, creates an environment in which opportunities for expression of personal growth, change and emotional responses become limited. Taking an autoethnographic, multi-method approach, the paper looks at examples in my own work with hip-hop group, Stanley Odd, that focus on personal, reflexive commentary as opposed to cultural or social commentary. Through the analysis of three songs released between 2012 and 2014 this article describes creative tactics and responses designed to push at the boundaries of hip-hop culture, Scottish culture and global culture to navigate and circumvent restrictions on emotive responses.