The Challenges In Writing A Memoir

How writing my first memoir was different than my previous New York Times Bestseller.

My first book was easy to write. It was facts and figures. It was the nuts and bolts of travel. Do this, go here, sleep here, use this company, save some money.

The problem was that this spoiled me. Because when it came time to write my next book, I decided that I wanted to do a memoir. I wanted to tell stories, give people a glimpse of faraway lands, and inspire them to travel more.

I wrote one book, how hard can a second be?

Well, it turns out very hard.

Because writing something that tells people how to do something is very different than baring a piece of your soul. All books are hard, but writing about yourself, your most intimate and vulnerable moments, and having to look at your own life in the mirror? Well, it can almost break you.

It’ll help you understand that old joke that a real writer is someone for whom writing does not come easy. To that I would add that real writing does not come easy period. It’s hard. It’s blood, sweat and tears.

Like a lot of writers, I’m not used to writing personal narratives. I’m not used to writing about emotions. I simply write about the how of travel not the why. My second book was a really struggle because it was a completely new writing style for me. My first drafts contained all the facts about my trip but none of the emotional struggles I faced or the reasoning I went. There was no person in the story. It was simply a robot moving from scene to scene.

Every draft got easier as I got more comfortable writing about how I felt (and was sort of forced to by my editors). I have trouble being open and vulnerable but that’s what makes a good memoir.

Because emotion is a universal constant and that’s what people connect to. So you have to have it in your story. Whether you like it or not!

A memoir is not something to be done lightly.

You may think it’s easy. After all, you know your life. You know what happened. You’re simply retelling it, right?

And you’re right: the facts and figures of your life are easy to tell.

But how do you make it interesting? How do you turn it into a story that people want to read? One filled with interesting dialogue, people and situations?

One that captures someone’s attention over 300 pages?

That is a lot harder.

Good storytelling keeps people on the hook with more than a well written story. There are lots of well written memoirs I’ve found really boring. Ones filled with elegant prose and big words that bored me to death. We think it’s only the words that matter.

But it’s the emotion that keeps people going.

Emotions are universal.

The story you are telling is just the backdrop. What people will relate to is not what you did or what you saw but how you felt. Because everyone has felt that way before. That feeling will make them mentally queue up a memory they had where they felt the same way too. It will have them nodding their head in agreement as they turn to the next page.

The more people can connect with the characters in your story, the more they will love your book.

While every writer has their own advice, here’s what I think works in writing a memoir that connects with your reader:

Step 1: Write out your story linearly.

Get the story out there in the order it happened. That way you can get the facts and figures of your story on paper. This isn’t going to be the final draft and you’re going to need to edit it greatly but at least you have the framework for what will be your book.

It’s like building a house. First you put up the framework then you fill it all in.

This draft answer the big question of “what happened?”

Step 2: Print out the story and edit it.

You need to read the book as a reader. What’s it feel like to read your story as someone who is looking for story to pass the time? I don’t believe reading on your computer screen can convey that feeling.

Print out you first draft, grab a pen, and read and edit this first draft. Find the typos, the plot points that don’t make sense, the plot holes, and the spots that need more explanations. This process allows you to “see” the book and get a sense of each page that serves a larger narrative.

When you’re done, go back and put your edits into your word document. You’re going to lengthen and make your story a lot more detailed and interesting doing this.

Now that you’ve created a linear story, it’s time to turn it into something more resembling a book.

Step 3: Find a white board and plot out your story the way they do with movies.

First, begin with the question: what’s the pivotal moment of the book? If you don’t have some pivotal moment in your book, you can’t really do a story. Think about any book you’ve ever read. They follow a story that builds to one significant event where everything changes and that moves toward a conclusion.

What is your pivotal event?

For me, it was coming home. I didn’t get kidnapped, hurt, fall in love, or decide to settle down on the road. My big moment wasn’t really a “moment.” It was simply the act of coming home and realizing I didn’t like it. It was the emotional climax of the story.

After finding the point of where I wanted the story to build to, I could then figure out where I wanted to go from there and how I would end it.

That allowed me to re-arrange the events in a way to logically and emotionally built to the climax.

What I realized in this process was that my story was filled with changes to my personality throughout time.

So I moved the story around that jumped around a bit. It went back and forth from the present to the past.

Now, I was building a story that followed an emotional arc of a trip around the word.

Every book is going to be different but I’m a firm believer that if you can see the story unfold, you can mix and match it to a point that makes sense for your book. It’s like putting together a puzzle. It makes it easier to figure out when you can see the whole thing in front of you.

Step 4: Send it out to people for edits.

After you’ve figured out your story, rewritten it, send it to friends you can trust for an unbiased opinion. At this point, you need some time away from the book. You need other people to read it and find the plot holes and points that are not explained well.

When you’re writing a book, it’s sometimes hard to see the forest through the trees as you are deep into the story. Sending it to trusted friends for opinion gives you a break from the story so you can come back with fresh eyes and allows you to get another set of eyes on the book.

And that is very important!

Step 5: Take their feedback and rewrite it (again)!

Be sure to get really deep. Stories connect with people because they connect with people on an emotional level. That is what makes stories powerful. The connection. Think of any story you love. It moved you. So, in this version, be sure do go into depth.

This was really hard for me to do. I’m not a very emotional person so going into detail about my feelings is really hard for me and took a lot of drafts to get right but it is worth it at the end as it created a more personal and connected story.

Step 6: Print out again and edit.

See tip #2.

Step 7: Hire an editor.

Contrary to what you may have been told, your editor won’t provide hands on feedback like you may want or need. They aren’t going to go back and forth with a lot of edits. In two books over three editors, I’ve found you’re pretty much on your own until the final draft. So you may want to hire help. Hiring an outside editor was really helpful, especially since this was my first memoir and I wanted help on how to make it great. They were like writing coaches. They were instrumental in getting me to think about the narrative arch of the story and how to fill things in. they pushed me to write more in depth and get more emotional. The final version of the book is much better for it.

Step 8: Edit again.

Repeat as needed.

Step 9: Have people read it again.

See step #4.

Step 10: Rewrite again.

Everyone likes to talk about how Jack Kerouac wrote On the Road in one sitting but they all forget that he spent another two years editing.

Step 11: Let it go.

Eventually, you’ll need to let your book go and send it to your publisher for review and notes. Books are a work in progress and no writer I know is 100% happy with their book. There is always something you’ll reread and want to change. I was editing and rewriting mine until the very end. But eventually you just have to let it go. When you can read it and say “this is pretty good” and when your friends say “this is pretty good”, it’s time to let it out into the world. Don’t wait until it’s perfect. It will never be perfect to you.


You’re going to hate your book when you first start. Writing it will be a painful process. You’re going to want to take it outside and beat it to death Office Space style. You’ll go through draft and draft.

Writing a memoir will be very hard. I don’t know any writer who has found it easier. I’m sure it gets easier as you write more of them but your first book will take a lot of time and commitment.

But, with this strategy, I wrote a book that people tell me is quite good. And, while I probably want to still change parts, the fact that it’s a book people enjoy is the most that I as a writer can hope for.


My memoir, Ten Years a Nomad: A Traveler’s Journey Home, is now available everywhere books are sold.

Nomadic Matt

Written by

Nomad, vagabond, and author of How to Travel the World on $50 a Day. Showing people travel can be inexpensive in hopes of inspiring them to explore their world.

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