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Confessions of a Former Anti-Outliner

Please welcome novelist Matthew Norman [1] to Writer Unboxed today! Matthew’s first novel, Domestic Violets, was nominated in the Best Humor Category at the 2011 Goodreads Choice Awards, and his second novel, We’re All Damaged, was an Amazon bestseller. His new novel, Last Couple Standing, is available now. He lives with his wife and two daughters in Baltimore, Maryland and holds an MFA from George Mason University.

We’re thrilled to have him with us today to talk about something many of us dread — outlining — and how he not only survived the experience, but thrived because of it.

Learn more about Matthew by following him on Twitter [2] and Instagram [3].

Confessions of a Former Anti-Outliner

A couple of summers ago, when my agent sold my new novel, Last Couple Standing, she also sold my next novel, which I hadn’t written yet. Here’s a summary of the conversations that followed.

Agent: “Guess what! They want your next book, too!”

Me: “Wait, my what now?”

Agent: “Yep. And, they’ve asked for an outline.”

Me: “An outline? Come on. Do I really have to do one of those?”

New Publisher: “Yes—and we can’t stress this enough—you do.”

Here’s the thing, though. At that point in my career, which included three completed novels, I was firmly against outlining. My theory, based on nothing but my own gut instincts, was that committing to a plot before writing a single line of prose would be stifling. I had an analogy for it and everything. It’d be like setting out on a road trip while wearing horse blinders. Wouldn’t I miss all the cool, weird, hidden little things along the way?

To those of you reading this who just loudly called me an idiot, touché. Perhaps you’re done here, because you’ve already figured this out for yourselves. But, for the anti-outliners among us, I’m writing today to report that I was wrong. Outlining my next novel was one of the most productive exercises of my entire writing life. It was creatively exciting, legitimately fun, and it led to the fastest, most complete first draft that I’ve ever written.

Here are the steps that I took along the way. Hopefully, they’ll help you successfully outline and then write your next novel.


Many authors will tell you that the toughest part of writing a first draft is figuring out the plot. Something happens, and then something else happens, and then more things happen because of those first things, and then everything somehow fits together. I know; it can be overwhelming. I’m getting anxious just thinking about it.

The solution—aside from mood stabilizers—is to give yourself time to lay out the incidents and events that will make up the plot of your novel, and to acknowledge to yourself that those incidents and events won’t arrive in your imagination in any particular chronological order.

For example, let’s say your main characters are Jim and Amanda. You may know that Jim and Amanda will find themselves back in New York City toward the beginning of your novel. However, you may not yet know what will lead them there. You may also know that a lengthy flashback will appear in which an eight-year-old Jim breaks his arm at recess. However, you may have zero clue where that flashback will go in your novel. You may have your ending all figured out, but the important two or three events that will occur just before that ending may be a total mystery.

To embrace all of this beautiful randomness, I recommend using simple note cards. Here’s how it works. As you brainstorm ideas for incidents and events, write your ideas down, one event per card. And, remember, in this stage, there are no bad ideas, and chronology doesn’t matter. Every flashback. Every conversation. Every car ride, argument, dog attack, stolen kiss, trip down the stairs, chance encounter, pivotal embarrassment, drunken dinner party, and heated phone call. Everything gets a card. Then, once you have a nice, significant stack of cards to work with, spread them out on a table and begin arranging them in whatever order makes the most sense.

It may seem messy, and some of your cards will eventually be tossed out in disgust, but what you’ll be looking at here is the plot of your novel. You’ll begin to see what’s working, and, just as important, you’ll be able to identify and fill the holes in your plot.

Jim has just lost his job. Out of desperation, he reaches out to his old roommate who now teaches at NYU. That’s what leads Jim and Amanda back to New York. You just figured all of that out while staring at your note cards.


Now, with your plot shaping up nicely, it’s time to open your computer and start making your pretend people and fake events feel real. I recommend naming this document something creative and sexy, like, “Outline_v1” or “<Title>_Outline.”

Start by typing out your note cards in the order you’ve chosen. Before, in the Note Card Stage, you had permission to be all vague and “brainstormy.” Now, though, it’s time to dig in and get specific. That means that you’re no longer allowed to say something like, “Jim and Amanda have an argument and then a dog bites Jim.” Instead, you’re saying, “Jim and Amanda have a heated fight about exactly where to sprinkle Amanda’s dad’s ashes, the bleachers at Yankee stadium or outside Central Park. Then a corgi escapes from the nearby dog park and bites Jim’s ankle, tearing his only nice pair of pants. Now he’s stressed because he has a job interview at NYU in 20 minutes and his pants are ripped.”

Writing such specific details while outlining may seem limiting, but, I promise you, it isn’t. The work you do here will help provide context for when you actually start writing your first draft. And, as you do, if you’ve outlined well, you’ll find yourself writing more clearly and more precisely, because you’ve already done so much of the hard work up front. Instead of getting bogged down in the mechanics of your plot, you’ll be able to focus on who your characters are, how they sound, and how they interact with each other. You know: the fun stuff.


Because that’s the big knock on outlining, right? That’s why you were so scared of it in the first place. It’s too rigid. Too prescribed. Well, it doesn’t have to be.

Let’s revisit our road trip analogy from before. If you’re driving down I-95 and you see a ten-car pile-up in front of you, you’re not going to go speeding right into it, right? Of course not. You’re going to hit the brakes and find an alternate route. Same goes for writing your first draft.

Once your outline is set—your roadmap written—commit to its contents and trust that you’ve done good work. However, don’t be so maniacal about it that you refuse to adjust when necessary. If you have a great idea in the middle of writing chapter four that you hadn’t considered during the Note Card and Outlining Stages, go with it and adjust your outline accordingly. Or, if the opposite occurs and you find yourself horribly stuck in the middle of chapter thirteen, stop and consider finding another way.


The job of an outline is to help you write the best first draft that you can in, reasonably speaking, the shortest amount of time possible. However, no matter how brilliant, thorough, and thought-through your outline is, your first draft is still going to be…well, a first draft.

Consequently, some sections will be comprised of the best writing you’ve ever done. Other sections will be an absolute disaster. Halfway through, for no apparent reason, your character Jim will have his named changed to Steve. There will be way too much of some things, and not nearly enough of other things. One chapter will stop for no reason, there will be more typos than you can imagine, and, at some point, apropos of nothing, Amanda will become a redhead.

Don’t worry; this is all perfectly normal. You can fix it in your second draft. And then in your third draft. And, <sigh>, your seventh. In other words: you’re just getting started.

Have additional tips to share, or cautions, or stories from the trenches? The floor is yours. 

About Matthew Norman [4]

Matthew Norman (he/him) is the author of three novels. He lives with his wife and two daughters in Baltimore, Maryland and holds an MFA from George Mason University. His debut novel, Domestic Violets, was nominated in the Best Humor Category at the 2011 Goodreads Choice Awards. We're All Damaged was an Amazon bestseller. And Last Couple Standing was named one of the best books of 2020 by Esquire. His latest novel, All Together Now, will be published in June by Ballantine Books.