Numerous opportunities exist for successful careers in the fields of hematology and oncology. Trainees must choose between dedicated training in one or both disciplines, and between careers in private practice or academic medicine. Individuals who favor academic careers must decide between patient-oriented clinical investigation and laboratory research. This article addresses the factors that influence these decisions and inform trainees about critical elements of the training experience that foster successful career development in academic medicine and private practice. Counsel on employment opportunities is provided along with advice on evaluating the merits of employment offers.