Cheryl Strayed

Like many people, I first came across Cheryl Strayed through her column Dear Sugar on the Rumpus, though her identity was still a secret at that point. Sugar’s advice is so unsparingly raw, honest, and compassionate — I think I read all the entries the first time I came across one of them. One day at a bookstore when I couldn’t find Wild on the shelf, I skimmed through Tiny Beautiful Things, a collection of the Sugar letters in book form, only to find skimming through that everything was too familiar for the fresh read I was looking for at the time.

Strayed’s decision to hike the Pacific Crest Trail came after several tough years centered around the death of her mother, the estrangement of the rest of her family, the dissolution of her marriage to a man she still loved but couldn’t be with anymore, and a brief frolic with heroin. She happened to see a guidebook about the trail in a store, and it presented itself as something she could do to fill the hole in heart. Strayed wasn’t at all prepared to take on such a long hike, so she ended up with too-small boots and an overstuffed backpack and barely enough money to get by over the hundred days she allotted for the journey. But the symbolism of it is incredible: with her feet literally rubbed raw, her focus pared down to just putting one pained foot in front of the other. Though it’s an intense struggle for her and several ridiculously unlucky things happen to make it harder, at the same time she found more help along the way than other hikers do. Her experience is both harder and easier.

For me the especially interesting aspect to this book is that Strayed had a specific expectation of what her journey would be like and, while it wasn’t actually what she imagined, it was still the transformative experience she intended, just in a different way. How appropriate, as I approached this book with a specific expectation that it would really hit me, since some of the struggles in her life are things I can relate to; more so, I went so far to expect it could helpfully shed some light on the things I still struggle with now. And it did, but more in the sense that it showed me how much I’ve learned already and how far I’ve come.