This study examined the relationships among motivation to avoid failure, defensive pessimism, achievement feedback, and emotional well-being. The emotional well-being of defensive pessimists was followed for two years. Participants were 64 defensive pessimists who completed instruments that assessed fear of failure, behavior inhibition system, defensive pessimism, and well-being. Structural equation modeling and two-factor growth model were used in the analysis. Results indicated that (a) there a satisfactory fit of the hypothesized model regarding the relationships among motivation, defensive pessimism, and emotional well –being; (b) fear of failure and behavior inhibition system have a direct effect on defensive pessimism, and high achievement feedback was associated with high emotional well being, and (c) latent growth model indicated that there is a decreasing trend in the emotional well-being of defensive pessimists during the two years. Results related to the nature of defensive pessimists were discussed.