Three Lessons From Cheryl Strayed

I recently had the honor and pleasure of hosting an onstage conversation with author Cheryl Strayed at National Geographic headquarters in Washington, D.C.

I’d never met Cheryl, and to be honest, I was worried that our talk might be stilted or awkward—that we somehow wouldn’t “click.” I met her 30 minutes before the event was set to begin, and after five had passed, I knew I had nothing to worry about. As Cheryl would later show onstage, she is so amazingly grounded, warm, open, vulnerable, honest, and articulate that I felt sure our conversation would soar.

The ensuing evening resounded with rich and layered lessons, but here are three that have continued to reverberate within me ever since.

1. “I couldn’t have gone in the right direction if I hadn’t gone in the wrong direction.” 

As all who have read Wild or seen the movie know, Cheryl hit rock bottom at the age of 22 after losing her mother, and attempted to obliterate herself with drugs and indiscriminate sex. She decided to hike the Pacific Crest Trail as a way to exorcise her demons and strip herself raw in order to rebuild a life for herself.

As she shared with me during our conversation, “Some people say my walk was an escape from my life, but it was the opposite—it was a way into my life.”

That statement alone was powerful enough, but then she followed it up by saying, “I couldn’t have gone in the right direction if I hadn’t gone in the wrong direction.”

At that moment I felt a wave of compassion, comfort, and hope flow through the audience. Such wise and empowering words! When we find ourselves in a bad place, whether on a remote trail or in the wilderness of life, we can get stuck obsessing about how we got there, wallowing in how miserable we are, or simply denying our misery.

What Cheryl did ultimately was embrace that bad place—she accepted it as the kick-in-the-butt precursor to the good place she got to, the wrong direction that enabled her to find the right path forward.

This notion, it seems to me, gives us all such hope. It underscores the fact that whatever trouble we may be in, whatever challenges we may be confronting or bad decisions we may have made, these are way stations on the path to somewhere better.

And it is up to us to get off the wrong path and find the right direction. The point is to not get stuck in the bad place, but to see it all as a journey—a long walk on a winding trail—and to empower ourselves to follow the compass at our core, to make our own map.

2. “You have to give yourself permission to enjoy your life after someone you love dies.” 

When I asked Cheryl to talk about solitude on the trail and what she had learned from it, she said that it had given her a much clearer understanding of her strength and her weakness.

I asked what her weakness was. After a pause, she said that her principal weakness had been that she couldn’t forgive herself for her mother’s death, that she somehow felt that enjoying life without her would be dishonoring her mother’s importance in her life.

Then she said, “You have to give yourself permission to enjoy your life after someone you love dies.” This was an ‘aha’ moment for me, when I realized that this was the reason and root of her self-destruction and eventual salvation.

As Cheryl had come to learn, you actually honor a loved one’s memory, their legacy, their vibrant ongoing presence in you, by living your life as fully and happily as possible. You show the world what you learned from this person whom you loved, and you apply those lessons to each and every moment, activity, and relationship in your own life.

After she finished saying these words, I felt a cresting wave of solace and gratitude wash over us, a room full of strangers-made-friends.

3. “Love and be loved. That is the purpose of life.” 

My last question of the night echoed the wonderful poem by Mary Oliver that Cheryl herself used as the epigraph to the last part of Wild: “Tell me, what is it that you plan to do with your one wild and precious life?”

The crowd was absolutely silent as they waited for her words. And with a radiant smile, Cheryl said, “Love and be loved. That is the purpose of life.”

Like much of the audience, I had tears in my eyes as she said these words. This is exactly my life philosophy, too, but to hear Cheryl say it, knowing the foundation of pain and hope and redemption on which these words had been built, touched me to the core.

Thinking about that moment and the evening as a whole, I realize that Cheryl embodies this truth and this goal, that her fully present presence—despite an overwhelming world of demands, commitments, and creations—fills the world around her with a hard-won love.

Don George is an editor at large at Traveler and the author of Lonely Planet’s Guide to Travel Writing. He has also edited several award-winning travel writing anthologies, including An Innocent Abroad. Follow Don on Twitter @don_george.