This paper analyzes the content of India's digital self-help gurus (SHGs), who are popular online figures in India, and engages a varied online audience across multiple social media platforms. We examine the role that the digital SHGs play to mediate cultural transformation following economic restructuring of the Indian economy that began in the 1990s and rapidly transformed the socioeconomic landscape. There was a shift to contractual and uncertain employment, and a simultaneous valorization of entrepreneurial citizenship. We propose that the digital SHGs facilitate this transformation by undertaking the work of mourning and the work of dreaming. Through their advice and content, they enable a letting go of the values historically attached with higher education and stable employment and help cultivate new attitudes toward skill accumulation, self-audit, and responsibilization—core tenets of enterprise culture—to posit entrepreneurial citizenship as a desirable goal. However, entrepreneurial citizenship can be exclusionary and offer unstable belonging. The digital SHGs assuage these fears and anxieties by normalizing failure and prescribing perseverance to cultivate the entrepreneurial self.