Rural extension is a highly complex practice. In general, the academic literature has studied the historical changes that have taken place in the extension approaches. However, little attention has been given to the study of changes in the extension workers’ approaches during their career path. In this study, it aims to describe how extension workers change their understanding of their role as a result of practice and experience. A total of 133 extension workers from six Latin American countries were interviewed. The interviews were transcribed and their content analyzed. The results show that extension workers, as a result of practice and experience, tend to (1) broaden and make more complex their understanding of extension work, (2) become aware of the limitations of their own knowledge and proposals, (3) adopt more dialogical and constructivist approaches, and (4) become more realistic. Besides, the research also shows that extension approaches are highly intertwined with the identities and the emotions of the extension workers, which explains why contributing to changes in how they understand their role is so difficult.