Winn has been published in periodicals such as Soul Journey, Campus Life, Leadership Journal, Radiant and Clear & Seven. He has also written for PreachingToday.com and for five years was the Deeper Walk editor for Relevant Magazine.

Winn's first solo book, Restless Faith: Hanging on to a God Just out of Reach, is a candid exploration into Winn's struggle to come to grips with the humbling, perplexing, riveting and mysterious nature of God. His second book Let God: The Transforming Wisdom of Francois Fenelon offers Winn's introduction to the wisdom of a warm, elder spiritual guide, just the sort of spiritual guide Winn craves.

Most recently, Holy Curiosity: Encountering Jesus Provocative Questions delves into the strange waters of a God who asks penetrating questions.

Winn, his wife Miska and their two boys live in Charlottesville, Virginia where Winn continues his writing and is helping to nurture the formation of a new church community, All Souls Charlottesville.