Guiding Gideon chronicles the encounters between Gideon, a young man in his thirties in the midst of crisis, and his spiritual guide, Julian. With Julian accompanying him to attend prayerfully to the life directly before him, Gideon traverses the troubled landscape of his interior life, where he encounters grace, his deepest wounds become sacred, and he is invited into fuller participation in the kingdom of God. Julian reflects prayerfully on each session, conscious that he is a privileged witness to the restorative movements of the Spirit within Gideon’s life and that the same Spirit is forming him in the way of Jesus. Guiding Gideon is for all who desire to become more attentive to their formation in the likeness of Christ. It is also for spiritual guides who want their mentoring, counseling, pastoral care, or spiritual directing to reflect and embody the way of Jesus. Written as a narrative, Guiding Gideon offers prayerful reflection within the context of guiding a fictional pilgrim and also invites readers to witness the formation of a fictional guide. Reflective of the contemplative vision of New Monasticism, Guiding Gideon models a prayer-action praxis inspired by Jesus’ Sermon on the Mount.