This article explores and compares the labor bifurcations of salaried and independent workers in contrasting labor scenarios that are representative of prototypical forms of employment currently widespread in Chile. On the one hand, that of a traditional department store which in the last decades has undergone a restructuring process that transformed itself into one of the most important Chilean retail companies. On the other hand, that of social innovation ventures, a form of business that brings together the entrepreneurial spirit with a declared interest in social problems. Through the theoretical tools of life-course sociology and biographical bifurcations, we analyze indepth 31 interviews to study the experience of workers entering a job category that differs from their educational trajectories and/or previous work. The results show that the experience of bifurcation varies according to the setting. While in retail there is an orientation towards adaptive preference, a valuing of stable employment, and dissatisfaction with the work they have to do, the entrepreneurship model shows attempts to shape one's own professional experience, which articulates with a precarious attachment to employment and an attempt to fulfill one's expectations at work. In the conclusions, we interpret the bifurcations of each scenario in the light of the transformations currently happening in Chile, seeking to establish their differences and similarities.