This qualitative research study identified the experiences and educational philosophies of mathematics teachers in an urban public high school framed by John Dewey's Theory of Experience and demonstrated by 21st century skills. To facilitate this process, the researcher used semi-structured interviews, direct observations, and collected lesson planning documents from five high school mathematics teachers. Content analysis was used to analyze this information and initiated the process of coding, categorizing, and thematizing words and patterns in relation to the research questions. The results of this study unveiled three themes. First, the context of the learning environment emphasized community expectations, a growth mindset, and standards-based grading. Second, the content in context entailed higher order thinking skills, peer and self-assessment through 21st century skills which the Partnership for 21st Century skills (2011) classified as learning and innovation skills, information, media and technology skills, and life and career skills. Last, student advocacy emphasized the advisory program, student leadership, and technology access. All in all, these findings uncovered a depth of knowledge driven by project based learning through 21st century skills. This study offered propositions for the future, which included continued research on educational philosophies, pedagogy, educational reform, and relevant professional development for the information age. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]