Our analysis in this paper deepens the scope of our earlier comparative work across regions by looking across employment groups, education, age, and gender, in detail in the Middle East and North Africa (MENA). Our specific focus on MENA confirms some expected results, but also yields findings that run counter to dominant narratives, as well as to what might be expected given the developments in the last few decades in the region. We find the unemployed to be systematically the group with the lowest well-being within any gender, age, or education group. However, male unemployed youth exhibit higher levels of well-being than the unemployed belonging to other age groups. This runs counter to the narrative that the frustration of youth was a likely catalyst for the 2011 Arab Spring uprisings. Prime age males in unstable work or in unemployment display lower levels of well-being. Within youth respondents, both full-time employed and unemployed women report higher well-being than their male counterparts under the same labor market situation – a possible partial explanation could be the lower stigma associated with female unemployment. What stands out is the complexity and at times unexpected manner with which people of different ages, gender, and education navigate labor markets in this complex and at times troubled region. Youth across all the countries report higher levels of optimism and life satisfaction than the common narrative suggests, Our exploration suggests a remarkable amount of complexity – and ability to adapt – among populations in challenging and changing labor market conditions.