Pearls of Wisdom (PoW) is a suite of computational tools and activities designed to engage learners in intentional reflection on their learning experiences. PoW supports the construction and sharing of Pearls, intentional-reflection artifacts containing project how-to information and refection on design and learning experiences. Pearls give learners an "objects-to-reflect-with" to make deeper connections between those meaningful and important ideas the learner has chosen to share. The collection of Pearls embodies the ideas and activities culturally resonant within the community. This diversity of perspectives may then be appropriated by other learners. The project goal is to evolve a community of practice around reflection and other deep-learning activities. That included reflection practices that emerged at both the learner and mentor levels. This work has culminated in the Cooperative Constructionism Framework, a guide for leveraging the learning potential of constructionist environments and expanding the constructionist-learning space. The study took place at the Flagship Computer Clubhouse, part of an international network of over one hundred after-school technology centers for youth from underserved communities.