Digital gaming communities are nuanced and developing. The eSports community has advanced in noticeable ways and represents the highest form of online competitive play for digital gaming environments. Due to the high stakes nature of eSports, its participants sit on the very edge of strategic planning boundaries and push the ceiling of developmental limitations of human capacity in digital game play. The skills developed overlap with several admirable career readiness skills in our Information Age (Hein & Engerman, 2016). The authors share the nuanced cultural habits of the eSports community and briefly overview connections to 21st Century skills development and career readiness.