How to take readers down rabbit holes they’ll follow and enjoy

Memoir authors are often concerned with how much to prioritize chronology. Should you roll out the events of your life in the order that they happened—chronologically? Is that too amateur a structure?

No, you can do it and sound professional, but telling your story strictly in order is probably not your best strategy. Even if you generally hold to the chronology, sometimes it feels natural to explain a little more about a topic that comes up. You find yourself going into the past to give the reader some background or jumping ahead to reveal how the situation was resolved. And then you may worry that it will be confusing for the reader.

No Rules, Full Freedom

There’s no one answer. A memoir is successful when it’s tightly written and keeps the reader turning pages. That’s obvious but still not easy to accomplish, and there’s just no rule book you can follow to make sure your memoir is a compelling read. Try to look at that in a positive way: it gives you the freedom to make your own rules for telling your life story.

Currently the trend is to begin your book at a pivotal point in your story. Create drama right away to get the reader invested in what will happen to you. After that, most authors cover ground that came before that pivotal incident, going back as far as childhood, but some write theme-based memoirs that draw from the entire time line as they cover each major point.

No matter what the structure, as you fold out your story you’ll likely find many times when you want to take a side road to focus on a particular topic or person. Stopping to follow the entire arc for that topic will save you from having to bring closure to that segment later on, when the topic itself is not as pertinent. Let’s look at a few examples.

Jumping Ahead

Maybe you’re writing about high school. You talk about a teacher who was helpful to you during a traumatic event or who was just an adult who influenced you in some significant way. Twenty years later, you run into that teacher and, in catching up, you learn that the teacher kept up on your progress by asking various people how you were doing. That encounter isn’t important enough for you to mention it when your narrative reaches that time in your life twenty years later.

But during the high school chapter, when you introduce readers to this teacher, it’s worth taking them down a quick “rabbit hole” to say something like: “After graduation I lost touch with Mrs. Jones and didn’t see her again until I was nearly 40, when I ran into her as I was doing errands in town. She knew all about me. She was candid about telling me she would periodically mention my name to people and ask them if they knew how I was doing. I took that to mean she still cared.”

Another reason to pause the chronology is to give the reader factual information that has little to do with you. Let’s say you talk about moving to a historic section of a city. As the years go on, you visit some of the landmarks and take visitors to the high spots, and each time the historic surroundings give you insight into your personal history. It can be cumbersome to say that as it happens chronologically. Instead, when you tell readers about your move to this new residence, you can go over some of the history, perhaps giving the city’s founding date, population and top tourist attractions. Within that context, you can inform readers of the illuminating effect living there had on your life. You may address a topic like this by both leaping ahead in your life and looking back in history.

Remembering the Past

At some points you’ll probably find the need to explain things about your past. A common topic is heritage. What were your parents like? When you begin your book from the beginning of your life, you can start off with your parents, how they met and some facts about their background. But if you start off at some later point in your life, you still might want readers to have information about your parents and general heritage.

This is when you’ll sharpen your segue skills. An easy way is to just devote a chapter, something like “My Parents,” and then you don’t need much of a segue—but you still need a reason to have that chapter appear. There are a lot of ways to create a segue. Consider:

• I wanted so badly to break down and cry, but the tears wouldn’t come. In that way, I guess I’m a lot like my mother. While Mom could be emotional in shifting to anger on a dime, I never saw her get the least bit weepy. I know she felt sadness, but her stoic upbringing taught her that crying indicated weakness. While she didn’t talk about her parents, I found out later that…..
• I wanted so badly to break down and cry, but the tears wouldn’t come. In that way, I was nothing like my father. No one else had a dad who cried in front of them. One time I found him sobbing…..
• One look at that car brought me back to the day I turned 16. My dad had brought home the same type of old clunker, thinking I’d be excited to learn to drive on a car that would be all mine. I thought Dad was so clueless, but my father loved us in his own way. He grew up as an only child in……

It takes some practice to go back and forth in time as you write what probably will be a mostly chronological memoir. You already know that the first draft of your memoir is just the beginning of a work in progress. It won’t take forever to finish your memoir, but it probably will take some rewriting and editing before you get it the way you want it. The chronology is an important piece, so be patient with yourself as you get the hang of flitting here and there in writing about your life.