In Chapter 5, readers get a chance to examine how social, organizational and cognitive advantages are assembled by students who look for strategic openings in learning and mobility. The chapter explains why disadvantaged students may benefit more in their opportunity-seeking endeavors if they decouple their learning motivations from those of their privileged counterparts. The chapter elucidates how some disadvantaged students benefitted from a strategic approach by synergizing social, organizational and cognitive powers. Yet, while transformative effects are periodically achieved through strategic endeavors, they tend to be transient, as utilitarian value is often short-lived. Being strategic does not inevitably create more opportunities in the long run. Moreover, the strategies of disadvantaged students do not necessarily bring about a more valuable result than the opportunistic approaches of their privileged peers. Furthermore, the processes of cognitive transcendence and social ascendance are often not interdependent or causative. At the same time, students who have engaged in cross-boundary learning often recount the transformative effects of these experiences.