DIY (do-it-yourself) craft is in the midst of a North American renaissance, and the reasons attributed to the phenomenon's meteoric rise are manifold. Thrift, conspicuous consumption, politics, environmental activism, nostalgia, individuality, community: each in turn has been cited as the driving force behind handicraft's recent blossoming. In this dissertation I examine the work of professional and semi-professional crafters through an alternative explanatory lens, one that is noticeably absent from academic investigations of DIY and underutilized in the scholarship on creative work at large: the rhetoric of pleasure. Through an examination of in-depth interviews with Etsy sellers and DIY bloggers, textual analysis of promotional materials from individual crafters and from Etsy.com, and participant observation at indie craft fairs and local knitting groups, I trace pleasure's effect on the chronology of commercial handicraft. First, drawing on Roland Barthes's distinction between jouissance and plaisir, as well as Mihalyi Csikszentmihalyi's concept of "flow," I argue that the pleasure crafters derive from the act of making DIY is itself bifurcated, at once concretizing and destabilizing their sense of self. I then direct my attention to the handcrafted object's sale, maintaining that both jouissance and plaisir are folded into the professional crafters' marketing narratives to build their personal brands and signal their creative authenticity. Finally I consider interactions between individuals in the craft community and the nature of the Etsy exchange, suggesting that commercial handicraft functions simultaneously as gift and commodity. However the primacy of pleasure throughout the sale of DIY obscures the challenges that creative entrepreneurship engenders. But in considering these oft unrecognized hardships--the loneliness and isolation; the endless administrative burdens; the pressures of a saturated marketplace--it becomes clear that there is a deep-seated irony at work: the more successful a maker becomes and the bigger her business grows, the farther away she moves from personally experiencing jouissance. I conclude by arguing that this paradox is emblematic of neoliberal creative work at large and points to the limits of the creative class thesis. I suggest that the surest path to the pleasures of creative production might in fact lie outside its professionalization.