This article first highlights how current technological developments and the transformation of professions are challenging education and the ability of schools and universities to train students to become tomorrow’s professionals. The article then analyzes a series of challenges and opportunities that the digital transformation brings to entrepreneurship education and coaching.The author emphasizes the importance of the trainer’s pedagogical choices, the learner’s personal development, and the need to include the different dimensions of human development in education. In the face of technological change and the transformations it brings about in society, the article also stresses the essential evolution of trainers, who must, beyond the continuous acquisition of technical knowledge, move from the role of expert who transmits knowledge to that of a companion in the service of a life project.