Participatory Design (PD) and service design have shown great potential in co-designing feasible solutions with marginalised societies. This study is part of a research project where dwellers in the informal settlement of Havana in Windhoek engage in context analysis for the establishment of a community centre offering technologies and services supporting the unemployed in finding work opportunities, self-employment and training. Participants first walked us through their neighbourhood pinpointing existing challenges they then communicated through persona sketches of local disadvantaged individuals like prostitutes and criminals. Societal issues, collective representations and sociotechnical gaps emerge, and participants reimagine these into work opportunities, enterprising, community cohesion, and overall alleviation and life improvement. The object of research is to align social realities, existing technologies, and design requirements to ensuring suitable usability, financial affordability, fulfilment of User Experience, and the ultimate self-sufficiency of community and overall project. This paper ultimately argues User-Created Persona (UCP) in PD as a fruitful inquisitive proceeding to explore and augment pervasive and smart work possibilities in locales with limited opportunity and resources.