Psychological momentum (PM) is construed as an extra‐individual phenomenon capable of elevating performance in a variety of achievement contexts including athletics, politics, and investing. Although generally perceived as a performance‐enhancing phenomenon, the present study tested whether one counterintuitive downside to developing PM is that it enhances risky decision‐making—by way of eliciting heightened confidence—within these contexts. Findings from one study support this prediction. Participants induced to experience PM prior to a card‐matching task with financial implications (chances to win $100 gift cards) made riskier gameplay decisions than those experiencing less PM. Critically, PM ratings were positively associated with task confidence, which in turn, mediated the relationship between PM and risk‐taking. Directions for future research and implications for decision‐making in sport, political, clinical, and investment domains are discussed.