Education is undergoing tremendous change. Technology and communication are central to this change, as speed and accessibility have increased exponentially. Learners' content knowledge is no longer as valuable as their "content navigation skills," and teachers' expertise is no longer beholden to didactic instruction. Education must accommodate this information age and the needs of undefined future employers. This article discusses a new approach to education known as the self-organized learning environment (SOLE) that is being utilized in northeast Ohio. SOLE offers a promising pathway through which to engage 21st-century learners through the integration of technology as support for the learner as a leader of his or her own learning experience, and transforms the teacher into a navigator, coach, and co-architect in that experience. Since its 2015 launch in northeast Ohio, SOLE Cleveland (SOLE CLE) has had a positive impact in formal environments (traditional classrooms) and informal environments (adult training programs, after-school programs, and professional development forums) alike.