Is it possible to use the written word, the language of painting, and social media technologies to explore sincerity in this day and age? In the body of work I have been pursuing since 2011, I try to connect these elements, using a DIY mentality, earnestness, and ideas drawn from the writings of Roland Barthes and W.J.T. Mitchell. This paper explores these concepts, as well as the self-portraits of Robert Arneson, Richard Prince’s series of joke paintings, and posts by artists from the website The Jogging. My paintings explore storytelling, which is central to my process of being honest and accepting of myself, as opposed to using irony as a form of detachment. Through an honest explanation of my process and decisions, I hope to provide further access into my work for my audience.