Resilience has gathered increasing interest among entrepreneurship researchers and practitioners alike. Even if resilience is often conceptualized as a resource that entrepreneurs draw from, it is also a result of entrepreneurial activity. In this study, we investigate how engagement in entrepreneurial activities contributes to the development of resilient abilities among youth. Different from research on resilience under adversity, we situate our study in a stable, advanced economy, where the development of resilience in adolescence may depend on opportunities to experience taking risk, confronting problems that entrepreneurs can solve, and from carrying one’s own choices and facing their—sometimes negative—consequences. By studying youth in a safe and stable Western society, Finland, we uncover how the development of resilience is related to engagement in entrepreneurship when the youth feel connected to their neighborhood and stay within institutional norms and rules. Accordingly, we unfold how engaging in uncertain, entrepreneurial activities may support resilience among youth.