The Woman Who Walked a Thousand Miles

This is The Storyof one woman’s rise and fall. It’s about how she hit rock bottom, and then blazed a trail to become a NY Times bestselling author.

And now… onto The Story

The man that said he loved her had a gleam in his eye.

He took her up and into his room, where they had been several times before.

He said he was excited to show her something.

She glanced around and thought he might have a gift for her.

Instead, he showed her over to a table.

On it, was aluminum foil, a lighter, and a pipe.

Her heart sank.

He wanted her to smoke with him.

She was alone, in a new town, with no money, and what felt like few options. Desperate, alone, and with no bright future pulling her forward, she agreed.

From that moment, her life became a nightmare, and she put one foot into her own grave.

Her life had always been complicated. But she had never been in so much danger.

Ten years earlier, she was thirteen.

It had been a happy time until she had to watch her parents’ marriage fall apart. Screaming and yelling became the norm. She watched her father beat her mother. It was almost impossible for her mother to leave him.

When her mother did summon the will to leave, she took the children and moved with their new stepfather into a small farmhouse. For the first few years, their house didn’t have running water or electricity. The girl didn’t mind, and it wasn’t until she grew up and moved away to college that her family got indoor plumbing.

During those years, her mother managed to hold the struggling family together. But there were many things that she couldn’t fix. From all outward appearances, the young girl was successful. She was a star cheerleader, ran cross country, and even won homecoming queen. To the people around her, it looked like she didn’t have any problems! But when she looked in the mirror, she hated what she saw. The faults she saw led her to isolation and eating disorders. Along the way, she used her achievements in school and sports to help numb her pain.

After high school, she was off to college. She was now the undisputed star of the family and able to excel in college where they had not. She didn’t get any handouts, and she had to earn everything along the way. At only 20 years old, she got married and began building a life with her new husband.

Industrious didn’t even begin to describe her.

She worked as an emergency medical technician, a youth counselor, a waitress, a temporary employee… whatever she had to do to pay the bills. She was all about hard work.

In her senior year of college, her world came crashing down. Her mother received a diagnosis of lung cancer, and the doctors discovered it too late. She watched her mother suffer a painful death. The one person who had been able to hold their family together was gone. Soon, the girl’s siblings drifted apart. A few years later, her once-promising marriage ended abruptly.

Now she was alone.

After a few months, she summoned the strength to begin exploring the world again.

Up until this point, she had done everything her culture told her to do. She’d excelled at school, college, and many of society’s favorite games. It felt like all the games she won led her nowhere.

Culture is stifling sometimes, but it can also protect us. As the girl broke free from the shackles of societal expectations, she soon found herself in the underworld.

She was 26, living in Oregon, and dating a guy who ran with a dangerous group of people.

She thought that she might be able to save him, and held out hope while they dated. At first, the relationship was fun and even thrilling

But on the day when he led her upstairs to that room and asked her to smoke heroin with him, her dream vanished.

In her suffering, she had found someone suffering more than her. Only this person wasn’t looking for love or redemption.

He was drowning and looking to pull somebody down with him.

She was never one to watch someone drown, and she kept agreeing to smoke with him. She soon found what felt like a temporary relief from all her problems. But there are tradeoffs for everything in this world…

She was struggling, and she started to realize that her own choices were making it worse.

That room. Her boyfriend. The pipe. His friends.

It was all evil. She was standing at the precipice of a dark abyss. With hardly any money, and she didn’t have any good plans to escape. But sometimes you don’t need plans. Sometimes you just need to cut ties and run like hell.

All she had was one crazy idea. It wasn’t much of a plan, but it was an escape route.

That crazy idea beckoned, but it also terrified her. She took stock of her current predicament. After careful analysis, maybe the idea was so crazy after all. Besides, the man she was dating, who should’ve been protecting and lifting her up… was trying as hard as he could to drag her down with him.

Looking back, she would say the reason for her escape was simple. For the first time in her life, she didn’t do something for society or her family’s approval. For the first time in her life, she decided to do something for her own approval.

Her crazy idea and escape route was the Pacific Crest Trail. The Pacific Crest Trail is a narrow hiking trail that runs along the west coast of North America. It stretches from Mexico up to Canada, along the way, it snakes through California, Oregon, and Washington. It is 2,650 miles long and takes around five months to complete on foot.

The massive challenge in front of her seemed impossible. Would it work? She had no idea, but she had faith that it was better than the alternative.

What if that escape and adventure made her into the woman she knew she could become? What if on that path she could reclaim the best parts about the little girl she’d once been? By making a choice designed to save and heal herself, she gained new powers. Her faith in the value of pursuing her own salvation drove her to take the first step.

So at the age of 26, without any prior hiking experience, she began hiking the Pacific Crest Trail. Along the trail, she learned what life in the wild was like. Every step of the trail taught her to endure uncertainty. Every step of the trail heightened her senses. In an environment where you must be present to protect yourself, your senses come alive.

At one point, she was walking past a farm. She thought nothing of it until she spotted a bull on the loose. The massive bull came charging right at her. The previous person she was might have panicked. But now, her senses were working on her behalf. She backed up against a tree, and blew the whistle she brought to help keep animals away. Against the tree, adrenaline coursed through her body and she blew the whistle as hard as she could. Soon, she ran out of breath, opened her eyes, and couldn’t see the bull anywhere.

She wasn’t sure if it was still lurking nearby or if it had left. Almost paralyzed with indecision, she summoned the courage to keep walking. Thankfully, the bull had grown irritated by the whistle, and that was the closest she came to danger on her trip.

At the end of 1,100 miles, she had a new outlook on life. She had safely escaped her past life, the toxic relationship, and her growing addiction.

Of course, her hike was risky, and most parents would call it “stupid.” But it’s far too simplistic to label her adventure and escape as just “stupid.” Sometimes, we only have two choices: the stupid option and the less stupid option. Sometimes, it’s only risky or riskier. She could have remained in her old private hell of addictive habits and people. Instead, she kindled the faith that she deserved more than a life of bad choices. She knew she had potential and went on an adventure in the real world to catalyze it!

As we go through life, sometimes we find ourselves in our own private hell. If you know you’re in hell, then you have to escape. Sometimes you have to literally run away and leave your old life behind. When you do, you have to realize that escape is risky, but the alternative of doing nothing may be far riskier.

As Carl Jung said…

We are doomed to make choices.

Life can be horrible. The suffering can be unbearable. And in those moments of pain, sometimes all we have to do is make the best choice we can see.

All we have to do is make a choice that does not make things worse. Over time, we can start taking small steps away from suffering.

The girl’s hike on the Pacific Crest Trail were the first steps away from making her life worse. They were the first steps towards opportunities that she never could imagine. When she began her journey, she was a struggling writer on the verge of addiction.

After her journey, she had earned a new level of real confidence.

As she recovered after her adventure, she began writing an advice column for a local paper. She started exercising and eating better, and it wasn’t long before she started dating someone new. She’d found a man who was what men should be….

After they dated for awhile, they got married and had children.

It would take her six more years after her marriage to finish and publish her first book, called Torch. It was a memoir based on her early life. It would take another six years after that before she finished her second book.

This book, you may have heard of. It’s called Wild. When Wild was published, it took off and debuted on the NY Times bestseller list. At the time, on the other side of the country, a new celebrity was looking to revamp her book club. That celebrity was Oprah, the book she picked was Wild, and she invited the woman who wrote it onto her show.

That woman was Cheryl Strayed. In a matter of months after that, Cheryl Strayed became a household name.

She made sacrifices, bet on herself for decades, and now she was in the promised land of opportunities.

Cheryl Strayed faced suffering, troubles, and struggle in her life. But she didn’t stop there and let them weigh her down. She transmuted them through her writing. That writing resonated like a lightning rod with people. Because she’d faced and overcome so much, her writing was like a magnet. She had created her own proving ritual of hiking the Pacific Crest Trail alone.

She went through the challenges and unlocked a life that many might view as a literal heaven. Now, she gets paid to write and create!

There is always evil in the world. There are always dangers. Sometimes they take the form of people who are drowning that try to take you down with them. Sometimes they chase us down like a bull. Sometimes those evils might even gain the upper hand and trap us.

When we find ourselves in the clutches of evil, we must have the humility to realize it. We must love ourselves enough to plot an escape route. The escape route might be the Pacific Crest Trail. It could be taking a new job across the country. Maybe it’s ending an abusive relationship. Maybe it’s leaving your parents house and beginning to live on your own in the world. Maybe it’s saying yes to a new business partner or investment. It won’t be perfect, and a life worth living is never without risk. Don’t worry about things being perfect. Take a small action today to make your life better.

If you’re brave enough, no matter where you’re at, you can always find the path to escape. You don’t have to make the perfect choice or have the perfect plan. All you have to do is just escape.

That’s her story, what’s yours going to be?

Thank you for reading this episode of The Story! We have an exclusive giveaway to celebrate Season 2 of The Story podcast — 2 free tickets to Salesforce Connections in Chicago on June 12–14th. Salesforce Connections is the digital marketing, commerce, and customer service event of the year. You’ll learn how to create personalized experiences at every touchpoint and deliver service that drives growth and exceeds consumer expectations. Head to and enter to win today. Thank you again to our presenting sponsor Salesforce for helping share these stories of business trailblazers who changed the world.

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