This paper reports on the findings of research aimed at examining the life stories of teachers who have experienced migration moves between Mexico and the U.S. and are currently engaged in English Language Teaching in Mexico. Drawing from a larger research project into the transnationals' learning trajectories in two Mexican states, the study presents three life stories to illuminate three broad transnationalism patterns leading to the achievement of different levels of investment in social, educational and professional practices. The paper uses a theoretical framework based on the interrelationship between transitions, identity, and agency to analyse how participants' interpretations of transnational experiences facilitate or hinder their engagement in social, educational and professional activities. Main findings support Casinader's (2017) perspective of transnationalism as a 'dynamic instability' showing that transnationalism is achieved differently by each of the participants. Participants' stories revealed that this has profound implications for their levels of investment since their subjective interpretations of life experiences played an important role in their levels of social, cultural and professional involvement.