The Cognitive Reserve (CR) hypothesis suggests that the brain actively attempts to cope with neural damages by using pre-existing cognitive processing approaches or by enlisting compensatory approaches. This would allow an individual with high CR to better cope with aging than an individual with lower CR. Many of the proxies used to assess CR indirectly refer to the flexibility of thought. The present paper aims at directly exploring the relationships between CR and creativity, a skill that includes flexible thinking. We tested a sample of 72 adults (aged between 45 and 78) assessing both their level of CR and their creativity. To evaluate CR we used the proxies commonly used in literature, namely, three subtests from the WAIS (vocabulary, similarities, and digit span) and the years of education. We also used an ad-hoc test asking people to report how frequently they tend to perform activities that are believed to increase CR. We used verbal creativity tasks (alternative uses and generation of acronyms) to assess individual levels of creativity. We asked participants to describe their main occupation (present or past) and coded each occupation as creative or not creative. Results (controlling for age-related differences) showed that scores from the WAIS correlated positively with creativity performance, even though correlations varied across the subtests. Focusing on the frequency and type of activities that people perform, and comparing individuals who have or had a creative job to those with a routine job, a clear relationship between creativity and CR emerged. This effect was more relevant than the level of job complexity. Implications for the study of CR and aging are discussed.