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!


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?

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