Image Credit: Alamy

Cheryl Strayed throws back her head and laughs when I ask her if she ever felt like quitting during her life-changing 1,770km solo hike along the Pacific Crest Trail through California and Oregon more than 20 years ago. Seated in a meeting room of the Intercontinental at Dubai Festival City, venue of the recently concluded Emirates Airline Festival of Literature, at which she was a speaker, she repeats my question: ‘Quitting? Yes, I felt like quitting almost every single day of the trek.’

It must have been punishing given that Cheryl was grieving her mother’s death, battling demons and completely unprepared for the walk.

‘See this,’ says the award-winning author, columnist and podcast host, raising her foot and showing me her well-pedicured toenails painted a bright shade of red. ‘The trek was so difficult that before the end of it, these toenails had all fallen off. It took months for them to grow back properly.’ I put down my recorder to take a look. Right now they appear none the worse for the wear and tear they endured trudging through snow, rain, gravel and sand for two months in a pair of boots a size too small.

Cheryl looks at her foot and her footwear – black open-toe wedges – for a few seconds before leaning back to talk about her walk and how it changed her life. Her feet and her footwear, incidentally, would figure once again later in our conversation.

For those who came in late, Cheryl was 26, married and pursuing a degree in English when her life went into a tailspin after her mother, Bobbi, died of lung cancer at the age of 45. Devastated and broken because she shared an extremely close bond with her mother, Cheryl neglected her studies and in search for comfort ended up having a series of hollow relationships. Her marriage crumbled. She started abusing drugs. She became pregnant.

Then one day, she shook herself awake. Hoping for a spiritual awakening to occur, the Minnesota resident and cross-country runner packed a backpack – a rather heavy one – slipped on a pair of walking shoes and headed off on a long-distance trek wanting to lose her rocky past and keen to find her real self. The walk became an adventure that would, 17 years later, result in a book, Wild: From Lost to Found on the Pacific Crest Trail (2012).

Cheryl with Reese Witherspoon, who played her in the film based on her memoir, Wild Image Credit: Alamy

An instant bestseller – it remained on the New York Times bestseller list for over a year – Wild was optioned by Reese Witherspoon and adapted for the screen by Nick Hornby with Reese playing the role of Cheryl. The film received two Oscar nominations and made Cheryl a household name, not only among adventure enthusiasts.

Although Cheryl authored three other books – Torch, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar, and Brave Enough, all bestsellers – and is a columnist for the New York Times magazine and Washington Post magazine, it was Wild that resonated with readers profoundly while garnering critical acclaim. If The New York Times called it ‘a classic of wilderness writing and modern feminism’, the Guardian said ‘a quiet dignity inhabits the heart of this book’.

Cheryl smiles when I mention this to her.

‘I didn’t want the book to be about me,’ says Cheryl. ‘It was not ‘hey, look, I’ve just had this adventure’. Nobody cares about me going on an adventure. Nobody cares about my mother’s death. That’s my story.

‘The writer’s job, the memoirist’s job, is to use the experience to tell a more universal story. So when I realised I’m writing about how we bear the unbearable, suddenly the story was about everyone because everyone has had to do it at some point of their life. That’s why people around the world relate to it.’

That was also the reason Cheryl’s session at the Emirates Literature Festival – where she spoke about the life-changing journey and the book that came out of it – was a total sell out.

‘I’ve never been a thrill-seeker,’ says the author, when I ask her what made her embark on the trek. ‘I’ve never wanted to jump out of an airplane or go white-water rafting or go bungee jumping to feel like I’m alive. The adventures I seek are of a quieter nature – like walking through the woods.’

The author, who Oprah Winfrey chose to be the guest at the launch of Oprah’s Book Club 2.0, admits that she went on the hike because she had been struggling in life. ‘My mother had died young, I didn’t have a father, I felt lost and sad and alone in the world. I needed to take the walk because I felt instinctively the need to find my strength again, and [I felt] walking alone in the wilderness would give me that.’

Having spent four years after her mother’s death veering dangerously off course, Cheryl wanted to make a clean break from it all. ‘I was hoping for a spiritual awakening to happen; I think it did happen but not the kind that I had expected it to be before I went off on the hike.’

Cheryl expected ‘a glorious epiphanous moment of healing’ after which everything would be OK. Instead, she experienced something deeper and life-changing. ‘It was not an epiphany and everything-is-better-now moment, but rather an understanding that I could carry my suffering with me, that my grief would always be with me, that getting over it was not about letting it go and leaving it behind me but learning how to carry it.’

The trek taught her several lessons not least how to get her life back on track.

Her preparation for the trip, though, was rudimentary – reading a guidebook on hiking the Pacific Crest Trail. ‘Remember, this was in 1995 so in many ways it was quite like the stone age when it came to the internet and online maps,’ she says. ‘All that I had was a guide book and my own ideas of how to hike.’ However, when she began her trek, she quickly realised ‘there was a lot to learn’.

The plan was to hike for about three months – it takes about six months to trek the entire trail – mainly because her financial situation was not rosy. ‘I didn’t have enough money and could not take off from work – I was a waitress – for so long. Plus I had a student loan to pay off.’

During the first eight days of the hike, Cheryl, who adopted the quintessential second name Strayed, did not see another human being and the only conversation she had was with herself. ‘I kept a diary writing at least once a day. When you are writing, it’s like having a conversation with yourself.’

She insists that she kept the journal not hoping to use it some day to write a book. ‘I’ve kept a journal all through my twenties and thirties and when I was on my walk, I documented it because that was the way I talked to myself. I love to do that.’

Years later, though, when she decided to write about her experiences, the journal proved useful. ‘The journal was a huge help. I could refer back to it and say ‘Yes on this day I met this person’, ‘on this day this happened to me’, or ‘on this day this was how I was feeling’.

‘Although I must say almost half of my journal is of me complaining about how my legs are aching and how raw and calloused they have become.’

While callouses, torn nails and a sore back from carrying a heavy rucksack were her constant companions, there were quite a few occasions when she was forced to forget about them and trudge on – sometimes even run – if only to survive. ‘One of the really scary moments was when, on a searingly hot day, I ran out of drinking water,’ she says. Trekkers usually carry a few bottles of water refilling them from streams, creeks or water tanks that dot the trail route and are marked on the trail map.

‘I’d exhausted my water supplies and was relying on finding water in a tank that, according to my map, was about half an hour away. But when I arrived, I was shocked: it was empty. That was really, really scary because I had absolutely no water and the next tank was some five miles away. It was a life-threatening moment.’

Thirst was not the only villain. ‘There were some terrifying moments when I came upon rattlesnakes and bears, too. Believe me, running into a very large hairy bear looking straight at you can be very, very unnerving and scary.’

Despite the dangers and the physical pain, what kept Cheryl going was her thirst for challenges. ‘I’m drawn to challenges… constantly drawn to them. Anything that requires you to push on beyond a point of comfort I am drawn to, unfortunately,’ she says.

She lists writing, apart from long distance walking, that pushes her beyond her comfort zone. ‘Even as a child, I knew I was going to be a writer,’ says Cheryl, who, a couple of years after her life-altering long trek, graduated magna cum laude with a double major in English and Women’s Studies. ‘And every time I write, I wonder why I’m doing this because it’s so very hard. You need a lot of discipline. Hiking is like that too. And running.’

Cheryl believes such experiences can be profoundly gratifying and meaningful. ‘You don’t remember the easy things and you never forget the lessons learnt the hard way… the experiences that challenge you.’

Cheryl with her husband, Brian, and her children, Bobbi and Carver Image Credit: Alamy

To drive home her point, she offers examples: ‘For some people, the most meaningful experiences in their lives are raising children or having a marriage that thrives over many years. Those things, while taking a lot of sacrifice and hard work, can be deeply satisfying experiences. It’s not about ease but about the commitment doing the hard things.’

What is her most satisfying episode in Wild?

‘There’s an important scene that I really think is the heart of the book. It’s when I’ve purchased a backpack and stuff, checked into a motel and ready to begin my hike. It’s the first time I’m packing my backpack and I’m trying to get all the stuff into it. It’s essentially a comic scene because once it’s ready and I try to hoist it on my back, I find that I cannot lift it.’

Cheryl says that that particular scene affected her deeply. ‘I realised that on a deeper level that scene is really the meaning of Wild to me. I was all alone in this motel room and I had a backpack that I couldn’t lift but I had to. That became the metaphor for Wild because it is all about how we need to bear what we find unbearable; how to endure and carry our stuff.’

Another thing Cheryl also wants to carry forward is her fight for women’s rights. A staunch feminist activist, she once said ‘the real liberation of women is profoundly connected to the shoes women wear’. Does she still believe so?

‘Women have for long been valued for their appearance and that it is such a deeply ingrained thing. At a deeper level, the liberation of women is tied to us freeing ourselves from this notion that we have to be nice-looking to be powerful or smart or important or interesting. And it starts from the feet,’ she says.

‘At the most essential level, our survival is based on our ability to move. But women over and over again choose to wear shoes that essentially cripple them. Shoes that you can hardly walk in, let alone run.’

She recalls reading the safety booklet on the flight into Dubai that requested women wearing high heels to remove them in case there was an emergency situation and they had to exit the aircraft.

‘Does an airline have to point out that the shoes you are wearing are a hindrance to movement? They don’t have to say that to men because men wear practical, sensible shoes.

‘I’ll sign up to be the leader of that movement where we just say ‘If I can’t walk properly in those shoes or if I can’t run in those shoes, then I’m not going to be wearing them’, she says.

Cheryl looks down at her feet once again and examines her own footwear. ‘You think these have a bit of heel?’ she asks me, rhetorically.

I check out her footwear once again and tell her that yes, they do have a bit of heel. ‘But it’s not too much, really. And I can walk comfortably... maybe even run in them.’

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What were the lessons Cheryl learnt following her long walk?

‘An important one is that we can endure hardship,’ says Cheryl.

‘One brilliant thing about long-distance hiking is that it is always hard. Every day is uncomfortable. There is pain and tiredness. You are out of your comfort zone. But I realised that by putting one foot in front of the other, we can overcome those difficulties.

‘The second lesson was that I could live without my mother - much as I loved her and much as I felt I could never live without her. That hike reminded me of my own resilience, my strength.

‘Third, I had such a tremendous sense of gratitude for the fact that even in my worst moments of despair, I had made a choice that was good for me. And my ability to do that was connected to the good mother that I had.’

‘Lastly, acceptance. I think that is a very spiritual principle – accepting that our lives with the good, the bad, the difficult, the joy, the suffering, the triumph, the regret - and to feel grateful for all of that together. I think that is the meaning of wild.

‘You need to be surrendering to it and accepting it as a part of your life.’