This study documents the extent and cyclicality of self employment entry and exit flows by the trainees after the training program conducted in the year of 2009 - 2011; explores transition to and from self – employment. The crest of popularity among the youth for entrepreneurship is high but the where about of starting a venture seem blurred. Zynorique Initiatives is a unique organization which came forward in taking the first step to make a change for the unemployed youth’s. With the unemployment rate rising high every year, the need to create a livelihood opportunities was in great demand so with skill development conducted by Zynorique Initiatives with the partnership Government of Nagaland the following trainings were initiated. The methodology used by the researcher is through multiple case studies, the aim of the study is to explore whether the training program acquired by the trainees has equipped themselves with the skills and abilities to start up their own unit or to be employable in any field of competition.