Spiritual direction is an art that has returned to the life of the Church since the mid 20th century. From the beginning as the early church shaped it, spiritual direction has been anti-structural. This article aims to examine the practice of spiritual direction in relation to church communities and also within the context of social structure, and to suggest the necessity of the art in our time while emphasizing its anti-structural nature. Victor W. Turner’s theory of anti-structural rituals is used as the main analytical framework, and in particular the concepts of “liminality” and “communitas” are highlighted to describe the anti-structural character of spiritual direction. In this article, Turner’s understanding of anti-structure is introduced first, and then the anti-structural elements of spiritual direction as below are argued: First, the extraordinariness of the ordinary(separation, solitude). Second, antihierarchical relationships (trust, equality, friendship). Third, contemplative experiences (love, openness). Fourth, active passivity (emptying, filling). Fifth, a journey of uncertainty(dialogue, discernment). Sixth, the recovery of gospel(introspection, lowering of self). Finally, it is argued that the anti-structural nature of spiritual direction is based on Christ. This article concludes that with Christ who lived an anti-structural life as his foundation, spiritual direction is a journey which the church should take again today towards the kingdom of God.