This article addresses street vendors’ excessive working hours, poor workplace safety and security conditions, together with the illegal compensation they must pay to local authorities. The article also examines socioeconomic background, challenges and handling strategies, urban authority, street vendors, the activity’s contribution to operators’ livelihood security, and diversification strategies article’s background is to bring out the demographic and socioeconomic conditions of males and females and sort out various challenges faced in running business of street vendors in Dindigul Districts. Furthermore, 150 street vendors were surveyed through personal interviews, and primary data was collected through an unbiased questionnaire. In Statistical Packages for Social Sciences (SPSS), the researcher used bar diagrams, frequency tables, pie diagrams, regression and Chi-square. Among the skill sets of street vendors, the researcher assessed potentiality concerning the following skills such as negotiation, knowledge management, merchandising, resource management, finance management and customer relationship management.