We examined the idea that adolescents' perceptions of their mothers as using parental conditional positive regard (PCPR) to promote academic achievement are associated with maladaptive self feelings and coping. A study of 153 adolescents supported the hypothesis that PCPR predicts self-aggrandizement following success and self devaluation and shame following failure, which then predict compulsive over-investment. PCPR functioned as a unique predictor of maladaptive self feelings and coping also when the effects of perceived parental conditional negative regard or psychological control were controlled for. The findings suggest that the experience of one's mother as using conditional positive regard to promote achievement leads to a non-optimal self-esteem dynamics, in which people vacillate between feelings of grandiosity following success and self-derogation and shame following failure, which in turn promote a rigid and stressful mode of coping. Thus, the practice of PCPR, although seemingly benign, appears to carry significant emotional and coping costs for adolescents. (Contains 2 tables and 4 figures.)