Kierkegaard’s pseudonymous work The Sickness unto Death belongs among his most popular and most commented works. Throughout the 20th and 21st centuries, numerous philosophers paid close attention to the theory of selfhood systematically expounded in this work. The study examines the critique of this theory formulated by Romano Guardini in a series of essays published in the 1920s. Guardini’s critique is an important contribution to the German mid-war debate on the nature of Kierkegaard’s philosophy and continues to provoke scholarly reactions even today. It is, therefore, relevant to study Guardini’s arguments in detail in order to see whether his definition of Kierkegaard’s theory as “dynamic personalism” is tenable.