While many public figures and civil society members perceive irregular migration as the source of various problems that modern societies encounter nowadays, this paper argues that this form of migration is rather the output of an outdated international system. The latter tends to protect the modern societies by enforcing the borders of nation states and leaving the most disadvantaged individuals on the wrong side of state frontiers. Thus, irregular migration is a complex phenomenon that one needs to approach critically at both macro and micro levels, in order to understand its origins and find the means to address it. Warsan Shire, a Somali poet who tried to explain the migrant crisis that the Mediterranean region has been witnessing for decades said: “Nobody puts his or her kids on the boat unless the sea is safer than the land” (Van Heelsum, 2016). His quote clearly highlights two realities that are attributed to irregular migration. It first shows the immensity of the hardships in the country of departure that oblige migrants to flee to another place where the living conditions are allegedly better. Second, it largely reflects strong aspirations among migrants to achieve their aim amidst tighter border controls and asylum policies that hosting countries impose to divert the migrant flows. In this research I aim to highlight how the aspirations shape and influence on the trajectories of migrants, by focusing on selected biographies of a diverse group of Syrian migrants who arrived in Norway. I explain how migrants react to various personal as well as other conditions that influence on them while they are experiencing different phases of (im)mobility.