Students explored the basics of painting through the use of skill building activities such as value scales, color mixing, and color matching. After becoming comfortable with painting, students took a self-portrait and posterized the image in Adobe Photoshop. This step helped to simplify the values in their portraits in order to translate it using paint. Once posterized, students enlarged their photographs using the gridding method. Carefully, students chose a monochromatic color scheme and completed their portraits by painting each value. This was a wonderful, low-risk, confidence building project for students that are learning how to manipulate paint.