Effectively educating for entrepreneurship is one of the challenges of the 21st century, and to do so requires a profound cultural change involving different sectors of education and operating in an inclusive manner. Such a renewal should emphasize creativity, problem-based learning and real-world experience. The aim of the present investigation is to assess the impact that the attitude toward the use of innovative teaching methodologies and educational technologies of a sample of trainee support teachers have on the promotion of entrepreneurial skills, in the classroom context, and how life satisfaction, sense of self-efficacy and attitudes toward inclusion processes act as moderators in the process. Methodologically, a cross-sectional study and the administration of a battery of self-report questionnaires via the google forms platform are planned; in particular, the following instruments are referred to: Intrapersonal Technology Integration Scale (ITIS); ad hoc questionnaire for the assessment of attitude toward the use of teaching methodologies innovative; ad hoc questionnaire for the assessment of perceived usefulness of the development of skills related to entrepreneurship in the school context. It is expected that attitude toward the use of innovative teaching methodologies and digital technologies is a predictor of positive perceived usefulness of the development of entrepreneurship-related skills in the school context from an inclusive perspective.