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In the rise of digital media platforms, individuals can engage in all three aspects of immaterial labor at once, including informational, emotional, and cultural work. Digital media has allowed influencers to embrace the maxim of do what you love (DWYL), such as working from home or creating vlogs (video blogs) while on vacations. The emergence of emotional and cultural labor shapes the concept of aspirational labor, which is defined as “a forward-looking, carefully orchestrated, and entrepreneurial form of creative cultural production” (Duffy, 2015, p. 7). Referring to social media as a platform of aspirational labor, this post will examine the aspirational concept by analyzing these three key features: productivity emergence, celebration of realness, and entrepreneurial self-branding.