How to Write About Personal Experience Like Cheryl Strayed

by Guest Blogger | 19 comments

Free Book Planning Course! Sign up for our 3-part book planning course and make your book writing easy. It expires soon, though, so don’t wait. Sign up here before the deadline!

This guest post is by Michelle Chalkey. Michelle is a Des Moines-based freelance technical writer and short story writer. Her work has been featured in Iowa Living Magazines, wordhaus, and Short Fiction Break. To read more of Michelle's reflections on writing and life, check out her blog.

Have you ever looked back on a piece of your writing and cringed? Not necessarily because of its quality, but because you realize you would write the story differently now that some time has passed. You realize you were impulsive in writing about a life-changing situation, that your views on the experience have changed after having the time to reflect.

Memoir: How to Write About Personal Experience Like Cheryl Strayed

As writers, we love to draw from our own real-life stories in our work. Whether in a memoir, a creative essay, or a blog post, we can be eager to document the experiences we go through.

Cheryl Strayed's Strategy for Writing About Experience

Bestselling author Cheryl Strayed is well-known for writing about personal experiences, with deep, prolific messages revealing themselves poetically throughout her memoirs. In her 20s, Strayed underwent a transformative experience by hiking 1,100 miles of the Pacific Crest Trail . . . by herself. Yet, she didn't write Wild, the best-selling memoir retelling her experience on the PCT, until 13 years later.

When asked at a recent speaking event why she waited to write the book, Strayed said:

“I didn't want to write about it just to say I did it. It felt clear that I shouldn’t write about it until I had something to say about it.”

Strayed makes a valid point. Would Wild have been as successful if she had written it at age 26, fresh off her hike? Would the memoir have had the same deep level of understanding and vulnerability that makes it so relatable to readers?

3 Reasons to Wait Before Writing About an Experience

Taking some time before incorporating an experience into your writing can leave you with a richer, more meaningful piece of work. Consider waiting to write about a personal experience for the following reasons:

1. We Say Things We Regret

It's easy to write out your steam when you're dealing with a break-up, a job loss, or any kind of rejection. You're still feeling the pain and you can only see the negative. Before you go posting about what an idiot your ex or your boss is, pour it out into your journal instead.

In a few years, you might be able to see the blessing that came from that rejection, allowing you to create a more well-rounded piece of writing on the topic.

2. Learn How Your Experience Can Serve Others

Strayed said she knew she had to write her story when she saw how it could help others dealing with grief and loss. Instead of bragging about an experience right when you accomplish it, wait until you see the message that lies a few layers in.

Yes, Strayed hiked 1,100 miles in 90 days without any training, but her story wasn't just one of physical accomplishment. More so, her journey was about overcoming the personal defeat of losing her mother to cancer. It was about having the courage to do the things that scared her.

And in sharing her story 13 years later, she saw how her experience of both emotional and physical suffering could help people who were struggling with their own grief.

“I knew I had to write about the experience the moment I understood it wasn't about me, but it was about grief and human truths.”
—Cheryl Strayed

3. You Gain a Better Understanding

As time passes, you begin to reflect on things differently. Things happen that remind you of your experience and make you see its whole truth.

Strayed said there are certain lessons she has had to be taught over and over again. We may have an inkling of what an experience taught us right after it happened, but when those lessons appear again and again they have more significance. Each time you make the same mistake, you get better at learning from it.

Ultimately, this repeated mistake shifts your initial view of your experience. You realize this lesson you keep being taught is the message you are meant to share with the world.

Your Personal Experiences Are Powerful

Personal experiences come in all forms. From the proud accomplishment of completing a marathon to the traumatic event of losing a loved one, there are lessons to be learned from the experiences that affect us the most.

Spend time getting your initial thoughts out in your journal, and be patient to let your understanding of the event develop. It might not reveal itself entirely to you for many years, but when it does, that is when your writing will leave the biggest impact on your readers.

Have you ever written about a personal experience only to change your views on it some time later? Tell us about it in the comments below!

PRACTICE

Set your timer for fifteen minutes and free write on an experience that happened to you at least five, maybe even ten years ago. In your free writing, answer the following questions: What do you realize now about the experience that you didn't see then? How have the lessons you learned from that experience showed up again in your life? How can readers benefit from your experience?

When you're done, share your free writing in the comments below, and check out your fellow writers' thoughts, too. Can you relate to any of their experiences?

Free Book Planning Course! Sign up for our 3-part book planning course and make your book writing easy. It expires soon, though, so don’t wait. Sign up here before the deadline!

This article is by a guest blogger. Would you like to write for The Write Practice? Check out our guest post guidelines.

19 Comments

  1. andrew

    true

    Reply
  2. Bruce Carroll

    Five to ten years ago? I can’t even remember what I had for lunch. Let me get back to you on this one.

    Reply
  3. Karley

    Young and little, as father’s temper grew brittle, my understanding was simple.
    Daddies scream and momma’s cry: and when things get mean, you hide.
    Tuck your feelings away way under the rug, and before long the troubles of yesterday will fade into dust.
    Never look them in the eye, it might hurt- you could die- and with luck, the truth will comply with this game of hide-but-don’t-seek.
    Many tears later, as time passed in years, I found that perceptions are fickle.
    Parents try their best, while their kids try next, but realize that not one method is best.
    It is up to you to confront the truth, but allow consciousness to take care of the rest.
    Don’t just burry your head away in the sand; learn how to fight, and remember to stand!
    Never give up, dust underneath all your rugs- and in time, you’ll know how to understand.

    Reply
    • Ayse Nur

      Your writing is really nice. 🙂

    • Michelle Chalkey

      I love that “hide-but-don’t-seek.” Beautiful writing, Karley, thanks for sharing!

    • Robert Ranck

      “It is up to you to confront the truth.”
      Karley, your words draw me in. It is pleasant to wrap myself in them.

  4. Topazshell

    It’s hard for me to connect with some parts of the past. These tough parts are the ones I would have thought simple to connect with in my mind and on paper. Then, there are other lives I’ve lived which come back easily. They beg for me to visit them over and over again with new questions and new solutions. I wonder if the past that is hard to connect with will become easier in time, or are some parts of ourselves locked away forever?

    Reply
    • Robert Ranck

      Connect with the past? Of course you can. Every memory, every special, secret moment is truly locked up and secured in our minds and our hearts. The trick is finding the right key. No matter how strong and impregnable the lock, the right key will bring the treasure forth. Sometimes a soft word or a gentle kiss will be more effective than a kilo of C-4.

    • Michelle Chalkey

      Well said, Robert! I agree. It may seem hard to connect to the tough parts of the past because we likely put up our own mental blocks that prevent us from going too deep with them. But like Robert said, you have to find the right key and be ready to open up to that part of the past. Maybe, when you’re subconsciously ready, the right key will just come to you.

  5. Kerri Reinbold

    Love this post! Thanks for the reminder that is our responsibility as writers to remain integral with our words.

    Reply
    • Michelle Chalkey

      Glad to hear it resonated with you! Thank you, Kerri 🙂

  6. theolivecat

    “A narrative crafted from spite is nowhere near as powerful as a narrative crafted from reflection.”
    I do know this though. A narrative crafted from spite is hilarious when you read it back later. You can get a good laugh at yourself when you go back and read that you truly hope that “crocodiles and alligators plague you and that your alarm clock never rings on time, leading you eventually to financial ruin.” We tend to say and think some crazy things in the thick of spitefulness and our thoughts tend to exaggeration. That exaggeration can be very humorous.

    Reply
    • Michelle Chalkey

      That is a good point 🙂 I think it’s good, probably even necessary to write out our initial feelings, but we might not want to try and publish those. They are indeed fun to look back on, and maybe that humor and exaggeration found in those initial reactions can fuel future writing in different ways!

    • Lola Palooza

      Honest-to-goodness spite really does make for the most well-rounded, flippant comedy insults. They just drip with venom and can be absolutely hilarious, as you said, yet utterly exquisite at the same time.
      Vent the spleen, spit the truth and have a good old roll around in the rich, syrupy goodness of being honest with yourself without apology.
      You can even make up fiction based on what you would like to happen, even if you know it won’t.
      You don’t have to publish it. You don’t even have to adhere to it. It is purely to make yourself feel better, and if you wish to reflect on it at a later date, have a rewrite (if you still feel strongly enough to write about it that is), and see if it still has legs.

  7. TerriblyTerrific

    Great article. Next time, I will definitely take my time to write when it come to a personal experience so that I can see it completely. Thank you.

    Reply
  8. Giulia

    This is the first time I have ever posted my work..
    Its a little long. I got carried away, the memory came to life.
    I’m looking forward to the helpful criticism!!

    My little hands were pressed against the foggy glass; I was watching the green blurs of the evergreen trees passed me. It was another typical day in Seattle, I would have never guessed that that day would change me forever. To this day I have a scar, I am internally stuck in the past, and may always be. I was warm within my car, papa was singing again some Amy Winehouse song, my younger brother was playing Mario cart on his Nintendo, and my oldest brother was listening to some Nirvana, and Red Hot Chili peppers on his I pod. These were the moments that fulfilled my childhood. The world was so simple back then. I could do whatever I wanted whenever I wanted to, I could create any world I wanted using my sweet imagination. I remember the beginning of that misty autumn day being joyful, I was with my family we were happy together, or so it seemed at the time. I was excited to go to the mountains in the backyard of Seattle, we were going for a bike ride, this time I was going to go troll hunting! I remember being restless in the back seat, I kept on asking mom if we were “there yet” and she kept on telling me close. It felt like time was repeating itself in that stuffy Subaru. I snuggled into my oldest brother’s warm arms, and convinced him to let me listen to his music, I liked his music very much, and there’s nothing more nostalgic than hearing that few 90s music on the radio for time to time. I fell asleep to the comfort of my brothers loving arms, and music, and woke up with my mother’s hand grasping on to mine, she kissed my forehead and said “Were here”. I unbuckled my seat belt, and I felt sleepy, I didn’t really want to go “troll hunting” anymore. “I don’t want to go” I told my momma. She picked me up, and placed me on the gravel ground, I instantly ran to papa with my bike, it didn’t take long for my energy to rekindle. Back then I was so enthusiastic, who knows what happened to me, if you knew me now, you would think life was like a vacuum that sucked away all the innocence splendor I had, and it kind of did. My family got prepared on their bikes, and I felt like such a big girl, because I got to ride in my own bike. I remember my younger brother challenging me to a race. I followed immediately behind his tracks, and off we went into the evergreen trees, biking together. It was foggy that day, there was the smell of mushrooms, and rain in the atmosphere mixed with the overpowering smell of the evergreen trees. The gravel was tough to bike through, and the sky was grey. It was magical. The speed at which I bikes at immediately turned the scenery around me into a green blur, as if I were in a dream…but this dream didn’t last long. I can’t explain to you the joy I had felt in those moments. I felt free, the wind would beat against my cold cheeks, and I felt like I was flying. There was nowhere I rather be in the world, I was truly happy. It’s as if my happiness was escalating so quickly and at an extreme intensity, that it could not be true. I looked up from my handle bars, and saw nothing. My brothers, my family they were gone. I knew they must have been a little bit ahead, and so I began to pedal quicker. There was a pain in my heart I never felt before, it’s as if I knew something was wrong. I was desperate, and weak, I had nothing to do but cry out for my mother. “ Maama!” I yelled, but there was no answer. A tear strolled down my face. I never felt such a cold tear in my life. “ Mamma!” I yelled again shortly after, my voice sounded like glass breaking. I started crying softly, and through my bike down, than sobbing, and coughing, snot conquered my nose, and lips “ mamma!” I screamed, in such a pitch that I swore I could feel the earth beneath me shake. Crows flew over my head, and started crowing, as if they were trying to copy my voice.
    I started running down the gravel path. The green blur turned red as I ran with my eyes closed, I tripped and fell on my knees, blood soaked my flowery pants, I laid on the gravel road crying, I stayed there unshaken, but I couldn’t stay there I ran again, feeling a stabbing pain in my side, there was a hill in front of me, who knows what my life would give me on the other side. It was my mother sitting just as unshaken as I was, she was next to my brother who was frozen on the floor, I couldn’t believe my eyes.
    I went to my mom, and asked her “Mamma what happened?”
    I couldn’t believe the words escaped my mouth
    She looked up at me, it was the first time her sweet almond eyes showed pain, it was the first time I saw the reality, the truth.
    Go get your father, her voice squeaked.
    I couldn’t believe what she told me. It was the first time I had responsibility. It was the first time something major depended on me. She reached her cold hand on my cheek, “Isabella I need you to be strong, I need you to go get your father”
    I looked over at my brother. There was no blood. There was his beautiful face, cold and frozen, his arms twitching, his voice groaning. He was in pain, and nothing ever hurt me as much as that recognition.
    Life is full of pain. I learned that day what it means to have someone you love in pain, how it hurts to see them suffer through life’s cruelty. It wasn’t his fault the spring of te bike broke leaving him flat on the ground with a concussion. I learned in times of sadness you need to be a strong girl, and defend your value against life, to be strong, and positive. Its important to look for a solution instead of hide.
    That day I lost a lot of my childhood innocence. It was the first major step of becoming a woman.
    Those forest used to be evergreen, but now they are everything but evergreen in my harsh memories.
    The truth is I am a weak girl, and the cruelties of life sink deep within my soul. I have not moved on. I wonder if I ever will.

    Reply
  9. vigabo

    I waited till I was 65 to write my memoir, “No Tears for my Father” about the childhood sexual abuse I suffered for 13 years. I followed that book by 2 more memoirs, one re my recovery and self-discovery of a person worthy of love, the other taking on my mother’s voice to tell her side of my story. I agree 100% that only by allowing years to distance myself from the pain of the past could I write all 3 books as I did, and as a result make them less a mournful journal of pain and more something that could help and encourage others to believe there is a light at the end of suffering if we take control of the pain instead of letting it control us. When we are ready to do that, we are ready to write our memoir.

    Reply
  10. drjeane

    When trying to think about something that happened five to ten years ago, the first thing that came to mind was my brother’s death. I don’t know if it has been long enough – it may never be long enough to think about this reflectively.
    The call came from a sheriff’s office in North Carolina, “I’m sorry to inform you that your brother is dead. ——– He was murdered. We think his wife may be involved.” The sense of unreality set in. Yes, they had been estranged from the family for about five years, but this was just not possible. Getting details via internet over the next few days added to the lack of reality. It hadn’t taken police long to see that his wife’s story of his coming home injured and her trying to revive him just wasn’t what had happened. Later we learned that she had beaten him to death with a hammer. She is now in a mental hospital – the ruling being that she is mentally unable to stand trial. If she is declared able to participate in her own defense, there may be a trial someday. Meanwhile, any understanding of what happened will not be forthcoming. It’s been seven years now and it still doesn’t seem real, except for the marble headstone in the country cemetery back home with his name on it. He simply should not be there.
    To address the questions in this assignment. Perhaps not enough time has passed. While I thought at the time that these kind of things simply do not happen to ordinary people, what I have realized is that of course they do – we are all ordinary people. We just hope it’s always some other ordinary person. I have learned to value even more open communication with family members. So many of us now wish we had gone to see what was happening that caused the distancing from the family. We somehow felt that by intervening we would make things worse. They were married for thirty years and my brother had gradually given up his life in an effort to “keep the peace.” First it was friends from before he married, then his home and other investments, and finally cutting off contact with his family. Perhaps readers might benefit from knowing that simply waiting and hoping things get better is not always the best approach.

    Reply
  11. Victoria Lau

    This is a wonderful article. I was inspired to write about my travel experiences like Cheryl, and worried that if I let too much time pass that I would forget all the details. This article has made me realize that there should not be any rush, and gaining a better understanding through long reflection afterward might be more beneficial.

    Reply

Trackbacks/Pingbacks

  1. How to Write About Personal Experience Like Cheryl Strayed – thomashwales - […] //platform.twitter.com/widgets.js “ A narrative crafted from spite is nowhere near as powerful as a narrative crafted from reflection. Tweet…
  2. How to Write About Personal Experience Like Cheryl Strayed – mrfernandogreen - […] //platform.twitter.com/widgets.js “ A narrative crafted from spite is nowhere near as powerful as a narrative crafted from reflection. Tweet…
  3. 2016: The Year in Writing - […] How to Write About Personal Experience Like Cheryl Strayed […]
  4. Stumped for Story Ideas? Try This One Tip - […] Cheryl Strayed calls this “following the heat.” Her most famous book is Wild, a memoir about the hike that…

Submit a Comment

Your email address will not be published. Required fields are marked *

Say Yes to Practice

Join over 450,000 readers who are saying YES to practice. You’ll also get a free copy of our eBook 14 Prompts:

Popular Resources

Books By Our Writers

Headspace
- J. D. Edwin
The Girl Who Broke the Dark
- Evelyn Puerto
Box of Shards
- K.M. Hotzel
44
Share to...