The decision to attend college is a question of human capital investment, yet resources to help practitioners frame human capital investment decisions remain elusive and few include the “gold standard” of finance: Net Present Value (NPV). Can one discuss human capital investment with an average adolescent using a traditional NPV approach? Motivated by this question, we presented 10 barriers to maximizing education-career NPV (e.g., clarity of costs, immature adolescent brains, individual discount rates, etc.). We outline an iterative, research-based approach to education-career investment, including framing the conversation, calculating paired NPVs, and structuring the decision. This multi-step framework leverages practitioner expertise to help adolescents consider important lifelong financial wellness implications of human capital investment.