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The Western cultural belief that individuals should “do what you love” for paid work is commonly appears in self-help literature for budding entrepreneurs. Facing competing devotions between work and family (and in this case, leisure), women may be attracted to self-employment, perceiving they do not have to choose and they can “do what they love.” I use modern roller derby as a case to explore the intersections between gender, work, and leisure. Surrounding the amateur sport is a modest economy of mostly women entrepreneurs selling goods and services specific to derby. These individuals are “doing what they love”—but at what cost? Conducting in-depth interviews with 28 roller derby entrepreneurs, I ask the following: How do roller derby participants make sense of their paid labor for the sport? How are these experiences gendered? I argue that while laboring for a passion brings intrinsic rewards, it is neither stable nor sustainable labor, as substantial financial support is needed, and passion plus the ideal worker norm drives entrepreneurs to be “always on” or always working. Furthermore, women may hold power as business owners, but this is limited to lower tiers in the industry (small businesses vs. corporations) and to within derby itself, not translating as well into other skating disciplines.