Many new tools and mediations are at today’s children’s avail that we couldn’t dream of when we were growing up. And yet, the millennium generation is also facing new challenges, which call for creative solutions. Today’s youngsters are growing up in a world increasingly shielded from nature; of ever more busy work and entertainment schedules; longer commutes; disappearing or reorganizing neighborhoods; and recomposed families. And yet the children are extraordinarily resourceful. They invent their own surprising ways of navigating rough seas and seizing opportunities. Much can be learned from their interests and genres of engagement. This chapter identifies six areas of change that seem to inform how today’s kids play and learn.