In uncertain economic times, who are those young adults that show positive expectations about their economic future? And who are those who worry? Based on previous stratification research and extending economic sociology insights into the realm of young people’s economic expectations, we focus on the impact of family class background and a sense of current meaningful community relations on young adults’ general and job-specific economic expectations. Analysis of Panel Study of Income Dynamics (PSID) data reveals that a sense of community belonging has a robust and positive impact on economic optimism of young adults, but the role of family socioeconomic background is weaker. We conclude that imagining one’s economic future is less about realistic calculation determined by early structural conditions but more about identity work of young people who assert their moral worth in how they imagine their economic lives and manage uncertainty and well-being in ongoing social relations.