This article reports on one of the modules of the Diploma in Translation at the University of Guanajuato in Mexico, called “Professionalization of Translation Seminar.” The program is of an introductory nature, while the sessions of this particular module are offered by professional invitees who have experience in various areas related to translation. Through integrating social learning, also called “observational learning”, into the pedagogical framework, the participants are presented with a broad range of professional contexts and conditions within the field with a double purpose: first, to recognize the complexity of the profession, and, second, as part of their comprehensive training, to guide future translators in defining their area of specialization and prepare them for the demands of the job market. Given the difficulties in maintaining a close and authentic relationship between teaching and professional reality in the area of translation, the lack of practical wisdom in the teaching of translation can result in an incomplete perspective of the multi-faceted nature of translation. In order to meet these challenges, the present phenomenological case study proposes the use of reflexive diaries as a source of analysis not only with the aim of fostering high-level metacognitive awareness among the students, but also to introduce them to the above-mentioned multiple facets that emerge as requirements in the professional profile of translators. The findings point to the successful implementation of a broad and diverse vision of professional experiences, which traditionally do not always receive sufficient attention in training programs of a more conventional kind.