Taoist doctrine had a great influence on Chinese art, and as a result, East Asian art appreciated the value of “Inaction nature(無爲自然)”. Inaction nature(無 爲自然) is related to Laozi's “Conforms to naturalness(道法自然)”, which is the doctrine that connects with Laozi's “The Greatest Skill Seems to Be Clumsy(大巧 若拙)”, it aims for poor beauty of “Inaction(無爲)” that goes beyond outstanding techniques. Laozi pursued the greatest skill that matched the nature of Tao and it is the skill of Tao(道之巧). Jol(拙) means ‘clumsy’ that is natural without any decoration. In order to ‘seem to be clumsy’, a skilled technique of “What the heart wishes one's hands accomplish(得心應手)” is required. Lee, Ki-woo(1921-1993) was a modern Korean calligrapher and engraver. He studied to Muho Lee Han-bok and Wichang Oh Se-chang, and tried to promote the artistry of engraving and calligraphy in the dark age of culture. By combining modern aesthetics on the foundation of “Clumsy and plain(古拙素朴)”, he boldly pioneered not only calligraphy but also the field of engraving, which was like a wasteland. He expanded the world of engraving indefinitely not only with stone engraving but also with various media. This paper sheds light on Lee Ki-woo‘s view of art, which was rose to the level of “What the heart wishes one's hands accomplish(得心應手)” and pursued “Purifying the heart(心齋)” and “sitting oblivion(坐忘)” and then reached to the level of “The Greatest Skill Seems to Be Clumsy(大巧若拙)”. I hope that this paper could be a cornerstone for restarting research on Lee Ki-woo, which has been sluggish.