The purpose of this review is to highlight the limitations of the traditional diagnosis/evidence-based symptom reduction paradigm and advocate for an individualized medicine approach that incorporates psychological and relational aspects of prescribing in addition to the objective patient presentation. Potential barriers, challenges, and proposed future directions for improving education in psychological and relational aspects of prescribing are discussed. Psychological aspects of prescribing, as recently spelled out in the field of psychodynamic psychopharmacology, are generally acknowledged as important, but they do not have a well-defined position in contemporary residency training throughout North America. While residents receive in-depth exposure to diverse aspects of what to prescribe in their psychopharmacological training, and they work with patients’ subjective and relational meaning and the quality of the therapeutic alliance in their psychotherapy rotations, an integrated approach to how to prescribe is generally lacking. Despite many legitimate challenges, the authors suggest that teaching an integrated approach that incorporates objective, subjective, and relational factors in the provision of psychopharmacology and utilizing evidence-based principles of individualized care should be prioritized in both residency training and the provision of psychiatric treatment as a whole.