Individuals sometimes exhibit judgmental biases that result in excessive risk-taking and suboptimal performance outcomes. Recent research has demonstrated that egotistic concerns about maintaining positive self-views can instigate judgmental biases and subsequent risky behaviors that undermine performance outcomes. The proposed research examines whether these biases and risky behavior occur more among people with fragile (as opposed to secure) high self-esteem, especially following ego-threats. Fragile high self-esteem involves favorable, but shallow, feelings of self-worth that are unstable (i.e., experience substantial short-term fluctuations), contingent (i.e., dependent upon meeting specific outcomes or standards), or paired with discordant low implicit (i.e., largely non-conscious) self-esteem. In contrast, secure high self-esteem involves genuine and well-anchored positive feelings of self-worth that are relatively stable, not contingent, and paired with congruent high implicit self-esteem. Two studies are proposed. Study 1 examines the role of fragile versus secure high self-esteem in overconfidence and risk-taking behaviors. Study 2 examines the role of fragile versus secure high self-esteem in risky decision-making as a function of myopic focus on reward.