The Project focused on self-reflection and insight, linking these processes to an artistic one – painting. As a way to respond to the research question: Does self-portraiture have the potential to guide us through self-reflection and insight? Workshops combining art and ways of thinking were designed and facilitated by the author, with the aim of improving the self-reflection and insight of students at LNU, based on theories of brain function and thinking. Using the workshop format, the author guided the participants through an experience of introspection through painting self-portraits. Areas of design included workshop, collaborative and critical design. A simple three-step design process was employed to create the Project, focusing on What, How and Why. Next steps included prototyping, designing the questionnaires which students completed, designing the art workshops, and advertising the workshops across campus. Results included nine respondents to questionnaires, four participants in the final workshop, and an array of findings regarding the self-reflection process and insight experienced by students through the design process. Although limitations were experienced, including a small number of participants, the results of combining self-portraiture and self-reflection and insight were mainly positive. It was concluded that this process could be proposed as a means to enhance self-reflection amongst students. Recommendations from the workshops included scaling up the process to include greater numbers of students and reaching an agreement with LNU to hold periodic self-portraiture workshops throughout the academic year, to enhance students’ self-reflection, insight and art skills. The author concluded that by holding workshops to paint self-portraits, along with exercises in self-reflection and insight, she had created a safe space for reflection. In future, students could be provided with guidance and support to use art as a platform for improving Self-reflection and insight, and at the same time enhance their art skills and potentially improve their well-being.