This is the story of a Black woman Baby Boomer who, inspired by the 1969 song Young, Gifted and Black, experienced cultural border crossings early in life. It includes reflections from Black women of the Hip Hop Generation who, decades later, also pursued the "world waiting" for them promised in that song. In our lived experiences across generations, we found strategic language use is part of the "gift" and critical to crossings. We also discovered identity implications as we "shift" across borders into predominantly White environments and back into our Black communities where language is perceived as a marker of racial solidarity. Black feminist thought is used to examine the implications of a communicative practice that has been done for so long and so well it appears effortless. But we know it is not—for both generations, there are benefits, yes, but also detriments, frustration, and fatigue.