This study explores the interplay between personal identity and entrepreneurial context in shaping the priorities and strategies of young aspiring entrepreneurs to achieve optimal levels of belongingness and distinctiveness. Challenging the conventional view that entrepreneurship primarily serves as a tool for distinctiveness, our research presents nuanced insights from in-depth interviews and reflective exercises with 44 entrepreneurs from startup and family business backgrounds. Our findings reveal that individuals who belong to personal identity types with high benevolence values, like the compassionate explorer, the conservationist planner, or the autonomous environmentalist, prioritize belongingness needs. In contrast, individuals with high achievement values, such as the generalist achiever, prioritize distinctiveness needs. Furthermore, we show how each identity type differs in its preferred belongingness and distinctiveness strategies, resulting in different entrepreneurial behaviors. We further highlight how the entrepreneurial context and family embeddedness provide distinct foundations for different strategies. These findings have practical implications for understanding and supporting the entrepreneurial journey of young individuals.