Sweden prides itself as a country where young women can enjoy gender equality. Yet many young women skateboarders still experience discomfort when skateboarding in public spaces. We argue that diverse strategies are required to intervene in the intransigent problem of gender inequality in the male-dominated sport of skateboarding. We discuss two intertwined strategies adopted in Swedish skateboarding contexts, strategic visibility and strategic entitlement. Strategic visibility is premised on making girls a special case, separated from the boys, and therefore highly visible. The other intervention goes beyond the limits of gender, aiming to achieve strategic entitlement, which takes-for-granted girls’ participation and competence. Drawing from ethnographic data, we explore the paradoxical spaces of these interventions, identifying the benefits and risks of each strategy. We conclude that both strategies are important, yet the latter breaks new ground. Strategic entitlement, which constructs skateboarding girls as ordinary and indistinguishable from boys, no longer constructs gender as a limiting factor. Interventions to promote gender equality should include strategies that seek to go beyond gender and strategies that acknowledge the significance of gender. We need to keep experimenting with and researching the unintended consequences of all strategies for challenging and changing male dominance in sport and leisure.