Cheryl Strayed Will Always Be Here for You

On the edge of Wallace Park in Portland, Ore., there is an unremarkable house with a camellia shrub out front. The house is painted a bluish gray now, but it might have been another color before. Cheryl Strayed is standing on the sidewalk in the rain with a smile on her face, conjuring a memory. This is where she took part in a yard sale in 1995, immediately after she—now quite famously—completed a 1,100-mile solo hike on the Pacific Crest Trail. At the time, she was a 27-year-old aspiring writer with 20¢ to her name. She sold whatever she could, including a pencil sharpener to a man who rode in on a bicycle. The man invited her to dinner with some friends, and later that night, Strayed met the person she would marry.

Strayed sees them everywhere: little signs, sm…