A classic distinction in the literature on achievement and motivation is between fear of failure and success orientations. From the perspective of self-worth theory, these motives are not bipolar constructs but dimensions that interact in ways that make some students particularly vulnerable to underachievement and disengagement from school. The current study employs the quadripolar model of need achievement (Covington, 1992; Covington & Omelich, 1988) to explore how these approach and avoidance orientations are related to self-handicapping, defensive pessimism, and helplessness in Eastern and Western settings. Although there have been numerous calls for research of this kind across cultures (Elliott & Bempechat, 2002; Jose & Kilburg, 2007; Pintrich, 2003), little exists in the field to date. In Study 1, with 1,423 Japanese high school students, helplessness and self-handicapping were found to be highest when students were low in success orientation and high in fear of failure. These findings were replicated in Study 2 with 643 Australian students and extended to measures of truancy, disengagement, and self-reported academic achievement. Consistent with self-worth theory, success orientation largely moderated the relationship between fear of failure and academic engagement in both cultures. These results suggest that in the absence of firm achievement goals, fear of failure is associated with a range of maladaptive self-protective strategies. The current project thus represents a unique application of self-worth theory to achievement dynamics and clarifies substantive issues relevant to self-handicapping and disengagement across cultures.