This paper reflects upon the underpinning principles of informal education and youth work practice via the philosophical lens of post-structural philosopher Jacques Derrida, by introducing notions of the trace, différance, justice and the gift. Once these philosophical themes are introduced, they are then applied to the underpinning principles of informal education and youth work practice, as introduced by Jeffs and Smith (1999, 2005), paying particular attention to notions of voluntary participation, democracy, fairness, conversation and well-being. The paper asserts that such philosophical consideration of theory, and practice, can provide further insight into important dimensions of youth work, such as how it has been historically difficult to evaluate such practice in a policy domain, as well as pondering the tensions between its principles and pressures to ‘professionalise’ its service. The paper concludes by asserting the importance of informal education and youth work as a form of an improvised ‘gift’, one that is difficult to be subsumed within an overly administrative rational ‘economy’ so as to inform discussion and debate in theoretical, practice and policy domains. The paper argues that the use of a Derridean lens opens up such discussions via new considerations so as to assert the importance of youth work endeavours that challenge economic rationality.