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Connected learning explains how people can build learning pathways that connect their interests, relationships, and formal learning to lead toward future opportunities such as careers. However, most learning systems are not set up ideally for connected learning; for instance, most schools still teach disciplines as discrete units that do not connect to students’ interests outside of school. We do not yet know enough about the structure of naturally occurring connected learning ecologies that do connect youth learning across contexts and help them follow pathways toward careers and other desired outcomes. Learning more about what works well on these pathways will allow us to design connected learning environments to help more youth have access to these desired opportunities. This paper analyzes two case studies of cosplayers –hobbyists who make their own costumes of media characters to wear at fan conventions– who benefited from well-developed connected learning ecologies. Cases were drawn from a larger interview study and analyzed as compelling examples of connected learning. Important themes that emerged included relationships with and sponsorship by caring others; unique pathways that start with a difficult challenge; economic opportunities related to cosplay; and comparisons with formal school experiences. This has implications for how we can design connected learning ecologies that support all learners on unique pathways toward fulfilling futures.