WATCH: The problem with calling out "privilege"

"Privilege" is an interesting word that can be easily dissected and applied based on perspective. The problem with using the term "privilege" specifically is that it has this existing meaning of wealth and well-connectedness and just being generally a part of society's elite. And for somebody who is white and privileged in that old sense, so somebody who is white and well connected, they hear "privilege" and... it fits in general. But I think when somebody like Bootstraps Guy hears it, he thinks "but I’m not rich." I think rather than honing in on this semantics point and getting him to say "I am privileged," it's more important for him to understand that society is structured in a racist way and to support policies that are just, rather than trying to get him personally to admit to a term that doesn’t really describe his experience.