What's at the intersection of race, color, gender, and family relationships? On the cusp of gender transition from female to male, Logan Gutierrez-Mock, a light-skinned person of mixed race, realizes he will soon be passing not only as a man, but also as a white man. He journeys to Mexico, the country of his grandfather's birth, a place where his own mother has never been, to search for connection with his family and his Chicano heritage. Through a candid interview at home and a visit to a street fair in San Francisco's famous gay district, the Castro neighborhood, Logan shares insights -- about acknowledging his white-skin privilege, challenging assimilation, and affirming identity -- that he gained from his travels.