The school principal impacts student achievement at a level second only to that of the classroom teacher. The USA and Germany are experiencing challenges in recruiting and retaining individuals for the principalship and the shortage is expected to intensify. Previous research has shown that increasing paperwork and responsibilities serve as inhibitors to entering the profession and that school principals are increasingly stressed by a wide range of responsibilities and a shrinking pool of resources. This stress causes physiological and professional difficulties that have a detrimental impact on school function and culture. The present study seeks to identify the major causes of stress, strategies for mitigating stress, and limitations of stress management among principals in the USA and Germany.