Graphology has been studied by scholars since 1870 through personality, forensic, and entertainment scopes. Researchers have demonstrated that handwriting analysis can denote certain psychological states and personality traits while also being an identifier of the original writer, but have not fully established the relationship between a person’s handwriting and their artistic skills. Searching for creative indicators in people’s handwriting can allow for clearer pathways to artistic careers and hobbies. The purpose of this qualitative case study was to test the hypothesis that artistic skills can be examined through one’s handwriting. A handwriting test was administered to 15 participants, which was then cross-examined with their artistic skills, level of expertise, and career paths. The results of these analyses indicated that there may be a correlation between a person’s handwriting and their artistic level but a higher survey pool would be required. Those interested in any artistic career field may benefit from the results of this study through self-administered handwriting analysis.