In this paper, we describe the findings from fieldwork conducted with low income youth in Nairobi in the context of a mobile phone based solution for employment in the informal sector. We utilize a narratives based approach to analyzing the lived experiences of our target demographic and present our findings in the form of design cues. In particular, we focus on the identity work conducted by our respondents, the barriers they face in accruing their livelihood, and the aspect of discontinuity in their employment, housing, and support systems. We present a set of design cues which are concerned with generating physical artifacts based on virtual activity, co-opting group dynamics, integration with government and civil society actors, and empowering the voice of informal workers. Our hope is to better align program priorities and delivery systems in accordance with patterns evinced from oral accounts of the intended beneficiaries.