This article proposes the use of therapeutic associative cards in career supervision. Associative therapeutic cards, as a stimulus material, can be used to elicit thoughts and feelings and to encourage communication with trainees. The aim of the study is to suggest and evaluate new and creative ways of closing the gap between theory and practice by demonstrating a possible implementation of associative therapeutic cards in career supervision. A scenario-based example is provided to illustrate how these cards could be used in the process. In addition, future recommendations, caveats, and the limitations of using therapeutic associative cards in career supervision are highlighted in order to shape the agenda of future research in validating such instruments using evidence-based studies.