Cheryl Strayed: From Wild To Brave Enough

In 1995, at the age of 26, Cheryl Strayed reached what she has since termed ‘the bottom of my life’. Grieving the untimely death of her mother some four years earlier, Strayed’s life had spiralled out of control, culminating in the breakdown of her seven-year marriage and that gut-wrenching feeling which is constantly present when you no longer know what you want or who you even are. 

Flash forward to 2018, and Strayed is an award-winning author with several appearances on the coveted New York Times Best Seller list. Her second novel, which arguably served as her breakthrough, Wild: From Lost To Found On The Pacific Crest Trail, was published in 2012 and has been translated into forty languages. It was also chosen by Oprah Winfrey as the novel with which to relaunch her book club. Hollywood actress Reese Witherspoon optioned the movie rights to the book before it was published, and starred as Cheryl Strayed in the 2014 film adaptation.

Following on from this, Strayed also published Tiny Beautiful Things, re-issued her first novel, Torch, and in 2015 published Brave Enough, a collection of quotes drawn from a range of her writings. What strikes me most about Cheryl Strayed’s story is that it took losing herself completely to eventually find herself. Wild documents her 1,100 miles (1,770km) hike along the Pacific Crest Trail back in 1995, shortly after her divorce from her husband. Despite having never been backpacking and with boots that were far too small and a backpack that was far too heavy (it wasn’t nicknamed Monster for nothing), Strayed’s experiences – and survival – over her 93 days on the trail, from California to Oregon (where she now resides) served to help her cope with loss.

Thirteen years after ending her hike at the Bridge of the Gods in Cascade Locks, Oregon, Strayed began writing her memoirs of the trail, which would become Wild.This March, Cheryl Strayed will be appearing at the Emirates Airline Festival of Literature in Dubai. I was therefore keen to get to know her better and learned how she finds writing and travel very similar, sought her advice on stepping out of our comfort zones, and discovered what she considers to be her proudest achievement. Read on to find out more, and to be inspired by her journey.

How did you change in the time between Wild and Brave Enough?

I think the biggest change in those couple of years between the publications of those books is that I went from being a writer who was known among a relatively modest orbit of readers and writers in the literary world to being someone “known”—to the degree we can know people we don’t know—by millions of people around the world. The reception of Wild brought me that attention and the experience was both thrilling and stressful. I learned so much in those first few years after Wild was published about what fame is, how to figure out which opportunities to say yes to and which to decline, and how to stay grounded in my real life, even when crazy glamourous things happen (like getting to attend the Oscars!).

How has your approach and notion of ‘adventure’ developed over the years?

I think I’ve always been of the mind that adventure can mean many different things. It’s kind of like beauty: very much in the eye of the beholder. Adventure is all about doing something that challenges you and leads you to discover new things about yourself and the world. Sometimes we do that on a grand scale far from home; other times we do it on a smaller scale right outside our front door.

Both are meaningful experiences, but my favourite fan mail is from people who write to me to say that Wild inspired them to take a walk for the first time alone. That’s an adventure if you’ve never dared to do that before, and it’s an important one because it almost always leads to more adventures.

Wild is taken from journal entries that you made throughout your hike of the Pacific Crest Trail. Is sitting down to journal something that you consciously make time for each day?

I wouldn’t say the book was taken from journal entries, but rather that I used my journal as a resource when I was writing the book. I had those raw pages to read when I needed help remembering specific details or wanted to see exactly what I was feeling on any given day. There were many pages about how my feet were killing me! But the structure of Wild is far more polished and crafted than my journals. I used to keep a journal all the time.

Last summer I was organising my office and I gathered together every journal I ever kept. They span from my teens all the way into my mid-thirties.I love having those records of years past, but in recent years I stopped writing in a journal. I stopped because of a combination of things: my busy life being a mother to two children and also the outlet that social media offers—the way we chronicle our days on those platforms–to some small extent replaces the reason I journaled. Starting at the beginning of this year, I decided to go back to journaling. It’s only been a month, but it’s fun to be writing longhand again in that more reflective, private way.

How does time in the outdoors affect your mental wellbeing?

There is no place I feel more whole and in harmony with the world. Even when things are hard, being in nature restores in me a sense of hope. 

How do you find the perseverance to keep going when everything seems to be against you?

The people who inspire me the most find beauty in every day, even when things are very difficult. They remain positive by remembering that almost always a way forward can be found.

What advice would you give to those who also want to write about their travel experiences, good and bad?

Story is powerful. Trust it. The best way to make your experience meaningful to others is to risk vulnerability. We see ourselves in others when they’re brave enough to truly show us who they are. Also, read lots of books and essays and stories by writers who achieve what you hope to achieve on the page. I learned to write by studying how other writers did it well.

What do you think about the rise of social media to document travels, rather than privately writing things down that you can then decide whether or not to make public?

I think social media has had both a positive and negative impact on most things—not just travel writing. On the upside, it allows us to immediately share our travels with others, in the moment. On the downside, it allows us to immediately share our travels with others, in the moment. It’s good to connect, to get feedback, to be able to stay in touch with others while we’re off on adventures, but it also takes something from us. That feeling of being truly alone, or at least temporarily away from most people we love and know.

I’m 49 and I consider myself lucky that social media didn’t exist when I was in my 20s, in part because so many of my travels during that decade were most importantly about finding my way alone and by dealing with the emotions that arise when there’s no one on your computer screen clicking “like.”

What is your definition of ‘Brave’?

cheryl strayed

Doing things because you know they’re the right thing to do, even if doing them makes you feel uncomfortable or afraid. This can be anything from telling the truth to travelling around the world.

If you could give any advice to our readers about stepping outside of their comfort zones and being ‘Brave Enough’, what would it be?

It’s important to get comfortable being uncomfortable because often the best things rise out of experiences that challenge us. Writing is my life’s work. You could say I love it, but my experience of it is very often one of agony.

Travel works the same way. So many of us idealise a trip before we go on it. We imagine all the great things we’ll do and see, but what we forget to imagine are all the things that will go wrong. The delayed flights, the illness caused by something we ate, the melancholy feeling that inevitably arises when you’re far from home and you wonder why you left at all. But those things—those discomforts or struggles—are the things that you will later treasure, or at least laugh about. They’re the things that make the experience meaningful. So my advice is to reframe the notion of “stepping out” of the comfort zone, which implies that the comfort zone is your default place. Make the uncomfortable zone your default. Step in.

What do you consider to be your proudest achievement or moment?

I’ve travelled a lot with my kids—it’s been really important to me as a parent to show them the world. I so deeply believe travel alters and informs and shapes us. In November and December of last year, my husband and I pulled our kids out of school for a couple of months to travel to several countries. We went to so many wonderful places, but perhaps the most meaningful was our time in Nepal, where we visited my friend Maggie Doyne who has a children’s home and school there in a town off the beaten track called Surkhet.

My children, who are 12 and 13, went to school with the Nepali kids while we were there and observing the grace and confidence with which they conducted themselves in an environment that was so very foreign to them made me deeply proud. They get all the credit, of course, but there was something about seeing them be comfortable even in the uncomfortable moments that made me feel like I’d achieved something too. Like everything I ever tried to give them, they got.

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