Chinese entrepreneurs, whose population has been steadily growing since the Reform and Open Up in 1978, are a diverse group of people. Though previous research has analysed Chinese entrepreneurs by special cases, few have conducted a nationally representative study of their typology. And even fewer have analysed the life outcomes of the different types of entrepreneurs. Relying on two waves of the panel data from the China Health and Retirement Longitudinal Study (CHARLS) and with the technique of sequence analysis, for the first time, we explored the heterogeneous career trajectories of Chinese entrepreneurs and their corresponding life outcomes. We successfully depicted four unique entrepreneurial trajectories in China since the 1950s, which are necessity entrepreneurs, employee entrepreneurs, persistent entrepreneurs and farmer entrepreneurs. Our empirical results can support both the cumulative disadvantage theory and the set-point theory in health-related studies. Among all the entrepreneurs, farmer entrepreneurs have the worst self-rated health in the long run, which supports the cumulative disadvantage theory. At the same time, all types of entrepreneurs have similar depressive symptoms and economic returns, which supports the set-point theory.