Knowledge on joining political violence let alone Islamist violence have in the past given more precedence to root causes as opposed to the more individual, contextualised dynamics of motivations. This paper explores one (of many) pathways of joining al-Shabaab by individuals from the coast of Kenya. It is based on qualitative empirical research, resulting from participant observation and conversations with former Kenyan al-Shabaab members. The paper demonstrates how decisions to join al-Shabaab were made as a result of this particular pathway.