Ever since the classic research of Nicholls (1976) and others, effort has been recognized as a double-edged sword: while it might enhance achievement, it undermines academic self-concept (ASC). However, there has not been a thorough evaluation of the longitudinal reciprocal effects of effort, ASC, and achievement, in the context of modern self-concept theory and statistical methodology. Nor have there been developmental equilibrium tests of whether these effects are consistent across the potentially volatile early-to-middle adolescence. Hence, focusing on mathematics, we evaluate reciprocal effects models (REMs) over the first 4 years of secondary school (grades 5-8), relating effort, achievement (test scores and school grades), ASC, and ASC × Effort interactions for a representative sample of 3,144 German students (M[subscript age] = 11.75 years at Wave 1). ASC, effort, and achievement were positively correlated at each wave, and there was a clear pattern of positive reciprocal positive effects among ASC, test scores, and school grades--each contributing to the other, after controlling for the prior effects of all others. There was an asymmetrical pattern of effects for effort that is consistent with the double-edged sword premise: prior school grades had positive effects on subsequent effort, but prior effort had nonsignificant or negative effects on subsequent grades and ASC. However, on the basis of a synergistic application of new theory and methodology, we predicted and found a significant ASC × Effort interaction, such that prior effort had more positive effects on subsequent ASC and school grades when prior ASC was high--thus providing a key to breaking the double-edged sword.