Youth workers are educators who play an essential role in the social, emotional, and academic development of youth in afterschool contexts (Fusco and Gannett, 2012; Pozzoboni and Kirshner, 2016). They build expertise on the job, learning implicit know-how through contextualized and relationally constructed practice and reflection (Polanyi, 1966; Taylor, 2007). The field, however, has under conceptualized how to foster implicit knowledge development in youth workers. Most youth workers learn experientially throughout their time in-service as they gain the skills and knowledge necessary to navigate complex dilemmas that arise in the field. Van Steenis builds on other scholars of youth work to argue that dilemmas crack open for the learner – who in the case of this paper are novice youth workers – tensions that exist at the nexus of their personal and professional identities. Structuring learning around “dilemmas” offers a key pedagogical move that affords the field a framework from which to build novice youth workers' implicit skills. Van Steenis takes a case study approach to present how and what four novice youth workers learned in their experience with dilemmas of practice, which were leveraged as a pedagogical in a higher education course called "Adolescent Development and Educational Psychology" (ADEP).