This paper explores entrepreneurial behavior crafting and its impact on their well-being. We specifically look at job and leisure crafting, motivations, and well-being outcomes. We use the identity-based needs of crafting as the overarching theoretical framework for our study and adopt a qualitative methodology to address the research question: How do entrepreneurs craft their work and leisure, and how does this impact their well-being? The findings show that entrepreneurs continuously craft their work to keep up with the uncertain and unstable work environment. Their freedom is significantly higher than that of employees. However, they have unique constraints in crafting their work, such as resources or other stakeholders (like co-founders, investors, partners, etc.). Their tasks are very flexible, but their responsibilities are higher. Relational crafting with different kinds of stakeholders becomes important in various instances. They keep cognitively reperceiving their work to make better meaning out of it or to improvise what they do. We further identify enablers and disablers in their work context. We also explore how their other domains of life impact their well-being. In doing so, we contribute to the work design literature by considering a unique work environment with differing constraints. We also contribute to the entrepreneurial well-being literature and bring in the need to understand their work characteristics in detail.