Sequential choices are ubiquitous in daily life, yet making optimal decisions in such settings--where properly accounting for option value is crucial--can be challenging. This paper provides field experimental evidence on the neglect of option value in high-stakes decisions and quantifies the associated welfare consequences. We study a centralized college admissions system where students submit brief preference lists. Although option value should encourage riskier top choices, many students are overly cautious and fail to include safer lower-ranked options. We argue that directed cognition--making myopic decisions while ignoring the value of subsequent options--explains this behavior. An in-field experiment targeting a key framing-based prediction shows that about 50% of applicants exhibit this pattern, especially among disadvantaged students. Counterfactual analysis suggests that de-biasing interventions could significantly reduce outcome gaps and improve overall efficiency. [Financial support for this report was received from J-PAL, CEGA, and BFI.]