Evelyn Underhill (1875-1941), best known for her book, Mysticism, was instrumental in popularizing this same topic in her time. However, it is a disservice to the prolific writer to reduce her to this summarisation. In the last twenty years of her life, Evelyn Underhill found a vocation as a spiritual director, becoming the first woman to lead retreats in the Church of England and speak to clergy about spiritual life. Through her personal letters, the testimony of her friends, and studying her notebooks, we become witness to a private spiritual journey which informed her unique ability to render the spiritual realm accessible to people from all walks of life. What one can learn from the life of Evelyn Underhill is that her efficacy as a writer and spiritual director was directly proportional to her own spiritual transformation.