Despite the strong educational and lay belief in the valency of global self-esteem, evidence of the effectiveness of self-esteem enhancement programs remains limited. The current study is a critical and empirical exploration of self-esteem in relation to anxiety, narcissism, and contingencies of self-worth. Self-report surveys from 92 young adults (43 male, 49 female, aged 23-37) indicated that self-esteem was negatively correlated with trait anxiety (r = -0.64) as well as to external contingencies of self-worth (r = -0.37), and positively correlated with narcissism (r = 0.38). Hierarchical regression analysis indicated that these factors significantly predicted 47% of the variance in reported self-esteem. The outcomes of this study challenge the notion that high self-esteem scores are necessarily reflective of overall psychological health. It is proposed that the conceptual basis of self-esteem requires revision within the framework of current psychological understanding.