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Failure can be defined as not meeting one's personal goal or standard in any realm of personal importance. With the present study, we assessed self-reported levels of failure and mental health variables, including measures of anxiety, depression, fear of failure, growth mindset, and hope. Our primary hypotheses were that more frequent early failure experiences would be associated with less fear of failure, anxiety, and depression, and that fear of failure will be positively correlated with anxiety and depression. The inverse relationship between frequency of failure and fear of failure was hypothesized due to the extant literature supporting exposure as a mechanism to overcome phobias. Our secondary hypothesis was that increased fear of failure would be negatively correlated with growth mindset, hope, and resiliency. Our primary hypotheses were partially supported. Counter to our primary hypotheses, we observed significant positive correlations between frequency of failure and fear of failure, anxiety, and depression. This may be partially explained by an unintentional retrospective memory biases in which depressed and anxious individuals are more likely to remember an inflated proportion of negative experiences. In line with our primary hypothesis, fear of failure was positively associated with anxiety and depression. Our secondary hypotheses were also partially supported. Counter to our hypotheses, there was no significant correlation in any direction between fear of failure and growth mindset. However, in line with our hypotheses, there was a negative correlation between fear of failure and hope and resiliency. Future studies should explore ways to most objectively measure past naturalistic failure experiences or focus on longitudinal research to measure naturalistic failure as it takes place and identify its correlates.