A primary goal of this chapter is to explore the phenomenon of increased attitudes and behaviors of entitlement among youth in modern America. With a basis that the increase is a result of social mindset shifts of post-World War II America, instances of the “Gimme More” mindset will be explored using qualitative research methodology stemming from the author's experiences and research as an educator. Moreover, the author will provide ways in which educators can combat this character-threatening mentality and help develop more accountable and empathetic citizens despite grade level, race, socio-economic status, and other elements that sometimes detract from a core issue and diverge from individual choice. This explanation will cover ideas that, if reflected accurately and consistently, can transcend to the human race, not certain races by exclusion or exception. While issues of intersectionality must be understood and discussed, they are not widely addressed in this chapter, and they do not ultimately thwart ambitions of global citizenship in the context that is explored here.