This chapter explores the early life of an entrepreneur who began working in their father's taxi firm at 14 amidst the social turmoil of Northern Ireland during the Troubles. It highlights their journey through economic challenges of the 1980s, the emergence of a strong entrepreneurial spirit, and the personal growth experienced while managing older taxi drivers. Reflecting on their work in the probation service, the chapter emphasizes the importance of empathy towards young offenders and the trauma that shapes their lives.