The increasingly ubiquitous digital (social/self) media and influencer economy reshape how people allocate time and consumption, which, in turn, alter individual educational/career decisions, relative returns across occupations, and resource allocation in the society. Educational pursuits exhibit stage-switch externality, intensifying short-run competition for skilled job placements but creating long-run strategic complementarity within job/service category (e.g., between investors and advisors). Multiple equilibria, including one featuring inefficiently low education, ensue. Individual education and occupational decisions depend non-monotonically on labor market search frictions and digitization. Greater entertainment surplus can discourage or even break down formal education. Entertainment influencers thus crowd out not only agents' attention but also education and work that facilitate efficient production (e.g., investments and public goods provision). A digital platform optimally raises the entertainment outside option and creator incentives, tilting equilibrium selection toward low aggregate education, with an ambiguous effect on equilibrium multiplicity. Regulations directly targeting influencers or reducing search friction in the labor market may backfire; taxing both influencers and followers, coordinating individual actions, and intervening in platform designs can mitigate inefficiency.