Within the depth-psychology corpus, modesty emerges as a term of considerable philosophical density, traversing I Ching hermeneutics, classical Greek philosophy, Christian asceticism, and analytical psychology. The richest vein of material derives from the I Ching commentarial tradition, where modesty (謙, Hexagram 15) is not a passive self-effacement but an active cosmological principle: heaven empties the full and augments the modest, earth elevates what is lowly, and the superior man carries modesty through to completion. Wilhelm and Wang Bi establish modesty as the ‘handle of character,’ the structural condition through which virtue becomes graspable and transmissible. Liu Yiming adds a critical corrective — excessive modesty tips into self-deprecation and injury to one’s inner strength, a warning that finds unexpected resonance in Esther Harding’s depth-psychological reading of modesty as a woman’s ‘fundamental instinct’ that can become a barrier to authentic creative self-expression. Plato’s Charmides opens a further tension: modesty and temperance are initially equated, then prised apart through dialectic, revealing modesty as contextually good but not unconditionally so. John Climacus transforms modesty into a dimension of humility, framing it as an ‘unassailable strongroom’ of the soul. Carol K. Anthony’s I Ching commentary integrates these strands into a depth-psychological frame, defining modesty as freedom from ostentation and ego-driven interference — a yielding to the Higher Power without inner resistance.