This chapter explores the paradoxical structure of cultivating Confucian humility (qian xun 謙遜) by juxtaposing it with the Chan 禪 Buddhist practice of the Three No’s (sanwu 三無) as articulated in Huineng’s 慧能 Platform Sutra (壇經). While Song 宋 Confucians like Cheng Yi 程頤 and Zhu Xi 朱熹 recast humility as an ethical ideal grounded in “non-dwelling” (you er buju 有而不居) and “no-self” (wuwo 無我), this chapter argues that explicit efforts to be humble can themselves impede the transformation they seek to bring about. I call this the paradox of striving for humility, a specific instance of what I term the broader paradox of practice, where intentional effort undercuts its own ethical aim. I then contrast this with a parallel paradox in Huineng’s thought: the paradox of striving for awakening, in which deliberate striving and methodical practice hinder sudden awakening. Juxtaposing these two paradoxes shows how both Confucian and Chan traditions wrestle with the limits of language, intention, and deliberate practice in self-cultivation.