“A luxurious chat from the beginning til the end, this is a wonderful chance to get to know Cheryl a little better and hear the voice behind the books. It’s a true comfort, which folds in everything from the power of walking and what it can do to you, the unfinished walk, the male narrative and damage on all sides, finding the ‘off’ button for our brains and whether such a thing is achievable, brainfog, her ‘Dear Sugar’ advice columns and discovering the human ‘standard set of problems’, and not being scared by the wilderness in which she grew. Lovely, and nourishing too.”

—Katherine May

Walking Through The Wilderness a conversation with Cheryl Strayed

When I was about to turn 30, and had never walked a mile on purpose, I decided to start training for a marathon. My back was against an existential wall. I was three years in to a Ph.D. and had just tanked my oral qualifying exams. Debt was mounting quickly. I was feeling physically, emotionally, and spiritually depleted and defeated. I was studying wide-awakeness and wanted to be asleep. So, I started walking. Now, at 51, I still walk. My pace is my pace. My stride is my stride. My race is my race. I learned all that from walking.

Walking is a part of wintering, for me. Wintering, as defined by Katherine May, is “a fallow period in life when you’re cut off from the world, feeling rejected, sidelined, blocked from progress, or cast into the role of an outsider.” More deeply considered, May views wintering as the cyclical, natural, ebb and flow of life. Walking is wintering in that, after walking for a while, my mind quiets. Walking is wintering in that I pay attention to nature — the bigness of it all — when I walk. Walking is wintering in that I return to my body with each breath and step. Walking is wintering in that it is an invitation to peace that is not a short cut around fear or sadness or chaos, but rather a path to stillness through it all. Walking is wintering in that I know I always come out on the other side a bit stronger.

Walking has taught me to see wintering as a gift. The gift of gently making my way through that which is before me. The gift of connecting with all that is — my body and the world around me. When I first started walking, my yogi/iron man coach would always say, “Run your race.” He was asking us to let go of judgement, doubt, and negativity and tune into our true selves, to something bigger. After many years, that makes sense to me. Walking, and by extension wintering, is the gift of learning to run my race.