The following work analyzes the main challenges faced by tattooed individuals during company s hiring processes. In order to achieve that, it was necessary to understand the characteristics of Generation-Y individuals and their choices compared to previous generations, besides analyzing this working generation s traits in an isolated manner. The evolution of tattoos since their creation, as well as the stigma created by society were studied, and so did the perception of the current use of tattoos as a form of expression. After data collection interviews were made, and the data cross-checking of the responses gathered and the theoretical references. Finally, at the end of the study, results were presented together with suggestions for further studies.