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This conversation with award-winning Canadian designer Shawn Kerwin explores the need for emerging designers to embrace risk and create their own opportunities for learning and professional development. Kerwin has designed sets and costumes for theatre for over forty-five years and has taught at the post-secondary level for over twenty-five. Her design work has been on stages across North America and across the world. While she holds a passion for opera and the classic repertoire, she has also been involved in numerous world premieres of plays and opera. As a teacher, she is passionate about helping students find their own creative voice and introducing them to the work of Canadian playwrights, many of whom she has had the pleasure of working with on new scripts. Over the past two years, in collaboration with the Charlottetown Festival and other organizations, she has mentored numerous young designers as they make the transition from being a student to becoming an active professional. She is currently exploring virtual costume design in an ongoing effort to continue learning and building her own skills.