Living in a society that abides by a binary system of gender with rigid definitions of what is masculine and feminine creates limitations on individual freedom of expression and gender performance. This can be especially detrimental to young children who do not abide by these strict rules. Little boys who like pink, wearing dresses, or playing with dolls tend to suffer the most at the hands of both child and adult bullies. Movies, television, and children’s books reinforce these stereotypes, while retail stories reflect our binary system with their gender unique clothing, toy, and party sections. Schools also enforce strict dress codes based on gender and some academic establishments design curriculum based on gender stereotypes. These powerful distinctions are all around us. By discussing the impact the gender binary system has had on my life as a woman and mother, as well as the personal experiences of other mothers through their storied experiences on social media, I explore this issue through a critical feminist perspective. Through my reflexive approaches of doing autoethnography, storying the experiences of others, and thoughtful engagements of feminist theories, I address the larger issues of gender performance in children and the interactions in which mothers actively engage in empowering their children to subvert gender performance by “normalizing” nonconforming gender performance for their children.