This paper presents an overview of the issues of labor market regulations in the Middle East and likelihood of comprehensive reform in the wake of the Arab Spring. The paper begins with an examination of the school to work transition for young people using data from four countries: Palestine, Tunisia, Jordan and Qatar. For Palestine, Tunisia and Jordan, the paper uses the International Labor Organization’s school to work transition data that were collected using similar methodologies across all countries in 2013. These data include young people aged 15-29 years old and asks a series of in-depth family background as well as work history questions. For Qatar, the study uses the 2014 Global Entrepreneurship Monitor data which includes a module on the school to work transition with questions modeled after the ILO data. Using various nonparametric approaches, this paper will examine how family background, demographic characteristics and educational background affect the work lives of young people. The paper will then consider the impact that potential changes in the regulatory environment may have on young people. The boom of the 1990s and early 2000s that was witnessed in several Middle Eastern countries largely bypassed the youth. Young people acquired more education than previous generations, but because their skills were not closely in tune with the needs of private sector employers (where much of the growth was occurring), education was not enough. Instead of working in the private sector, the tendency was for young people to queue for public sector jobs even though these jobs began to shrink in importance throughout the region. Today, post-Arab spring regimes will face many economic challenges. Primary amongst these challenges is the desire to quell the social discontent from the youth and others by making economic concessions while simultaneously reforming education and employment institutions that helped lead to the skill gap in the first place. This paper will examine the potential effect of a variety of specific labor market reforms and the likelihood of both their successful implementation and the success of similar efforts in ameliorating the disparities that exist in similarly rigid labor markets.