This teaching case aims to help undergraduate students in Business Management to reflect on decision-making for entrepreneurship, impacts of organizational decisions and entrepreneurial capacity. The case presents Eduardo's story, a young man with a job and labor guarantees, faced with the opportunity to change his professional career. However, he needs to analyze the market, his technical knowledge, and his skills to make an assertive decision. In this context, he faces the following dilemma: to remain employed, having his career defined by the employer and the guarantees ensured by law, such as non-variable monthly income, predetermined labor hours, vacations, among others; or undertake in the service provision sector through coaching, assuming all the risks and responsibilities of the enterprise. This case relates to decision-making and entrepreneurship.