Background: When people think that their efforts will fail to achieve positive outcomes, they sometimes give up their efforts after control, which can have negative health consequences. Purpose: Problematic orientations of this type, such as pessimism, helplessness, or fatalism, seem likely to be associated with a cognitive mindset marked by higher levels of accessibility for failure words or concepts. Thus, the purpose of the present research was to determine whether there are individual differences in the frequency with which people think about failure, which in turn are likely to impact health across large spans of time. Methods: Following self-regulatory theories of health and the learned helplessness tradition, two archival studies (total n = 197) scored texts (books or speeches) for their use of failure words, a category within the Harvard IV dictionary of the General Inquirer. Results: People who used failure words more frequently exhibited shorter subsequent life spans, and this relationship remained significant when controlling for birth year. Furthermore, study 2 implicated behavioral factors. For example, the failure/longevity relationship was numerically stronger among people whose causes of death appeared to be preventable rather than non-preventable. Conclusions: These results significantly extend our knowledge of the personality/longevity relationship while highlighting the value of individual differences in word usage as predictors of health and mortality.