Since the times immemorial it is a tendency of human beings to look at the towns and cities for a superior career stature and well-paid occupations. The crowd pulling factors of these urban landscapes are strong economy, plenty of opportunities and a sophisticated lifestyle which the rural front doesn’t offer. However, the reversal of trend i.e. people started to prefer the small towns or villages over the metro cities is throwing a new challenge to many stakeholders of the society including the administration. The job opportunities created by both service and manufacturing sectors at the urban arena are gradually losing the glory. The smaller towns, once overshadowed by their larger counterparts, are now emerging as attractive hubs for professionals and job seekers. In this paper the critical reasons are discussed viz. why people started choosing small cities offering small jobs and embracing the underemployment rather than going for better occupations with well pay at metros and cities. The eco system at urban front is an independent variable whereas the underemployment is considered as dependent variable. The paper discusses in detail ‘why people are accepting underemployment’ and ‘how the rapid urbanization pushing personnel towards the underemployment’ with the support of case studies. Here the parameter for deciding the underemployment is ‘hours or days of work availability’ and ‘the utilization of skilled possessed by individuals’ obviously affects the financial strength of the individual. The discussions in the paper highlights the lacunas in urbanization which is in fact creating the underemployment instead of better employment for those equipped with academics and skills. The observations showcased in the paper will be handy for the people to plan their careers in a strategic way. Simultaneously the game changing elements are revealed to the advantage of prospective entrepreneurs and established industry players.