Inside the game industry, we praise the outsiders and applaud their tremendous innovation, whimsy and creativity. We crave the freedom we perceive they have. Yet, outside the game industry, those who push the boundaries often feel quite alone, not certain if their ideas are worthwhile or worthless. They have neither parallel nor peer and crave the validation that comes from being inside. Inside wants out, outside wants in. In this talk, Romero explores this paradox, the struggle for self-validation and acceptance, and considers an inside/out outside/in path that works for all.