Creating Character Depth Through Confounding

The other day, I had lunch with a colleague, and he described an idea. He wanted to write a book with his wife, but with a fun twist. He would write one chapter, his wife would write the next, and so on, back and forth. Neither would get to see what the other wrote until it was his/her turn to take over the book.

Beautiful sugar skull woman illustration. Day of dead vector illustration.That got us talking about the genre of the progressive novel. If you haven’t heard of things like round robin writing and the exquisite corpse (see left for what I picture when I say that), well, they’re essentially vehicles for people to collaborate on a story or work of art.

Check them out. They’re fun, and as I’m seeing, they can be useful projects to use as inspiration in solo writing later. But first, creative writing class.

Confound It!

Our lunch conversation led to me remember one of my creative writing workshops. This one was called “Confound It!” or something like that. I might just be making that up. Whatever. If I am, I’m doing a good job because it sounds cool.

It was a collaborative writing exercise in which everyone would write a paragraph, pair up with someone, and switch papers. You would read your partner’s paragraph and write their next one. Except you weren’t supposed to be nice. Your goal was to confound your partner. You were to give them a paragraph that utterly changed the course of what they were writing and forced them to try to recover from whatever disasters you created.

So in “Confound It!,” paragraph one goes like this:

A young man sits and has a heart-to-heart with his estranged, dying father. They hash out old demons from the young man’s childhood. The son finally had the courage to tell his father he had felt abandoned by the old man his whole life.

Paragraph two goes like this:

Not far from the hospital, the abominable snowman, like the young man, was tired of a lifetime of rejection. So, using methods not described in this paragraph, he procured a cache of enriched uranium, and now we’re in the midst of a nuclear winter only he–and for some unspecified scientific reason, also flamingos–could survive.

Paragraph three goes like this:

Dude, come on.

Or maybe it goes like this:

Even the flamingos rejected the abominable snowman, and he learned that extracting revenge through violence was never going to fix the pain he felt inside. The young man at least died, albeit in a mushroom cloud, with a clear conscious after attempting to reconcile through conversation.

This is also kind of the plot of Frankenstein. See, I’m not a very good creative writer even when I’m plagiarizing.

But Confounding Yourself…

The last few Pulitzer-journey books that have graced my bedside table have reminded me of this exercise. These authors’ technique isn’t collaborative in nature, though. Thier goal seems to be to confound themselves. They carefully set up character development in one chapter and then completely undo their work in the next. But this isn’t bad writing. Or rather, it’s bad writing like a fox. (I’m not very good with simile, either.)

The first book that reveals this technique is Olive Kitteridge. In chapter one, we see a harpy wife nagging her sweet, mild mannered husband, berating him in front of guests and drowning him in a sea of “I cook for you, I clean for you, and what thanks do I get?” Olive is extremely unlikeable in this chapter. But in the very next chapter, author Strout undoes all that hard character work–or rather, she complicates it. Olive is a strong woman who knows exactly when people are in trouble. There’s a man in a truck who’s contemplating suicide, and Olive sees him and invites herself into the car. Even though he’s largely silent, she perceives what’s going on. What’s more, she deals with it in just the right way. She’s solemn and strong and doesn’t sugarcoat things. There are few words exchanged, but her curt observations about the world and his family were exactly what he needed to hear to feel less alone. We see that Olive has a soul, and it’s a soul capable of reaching out to others in a deep way. We can also sense that Olive has scars herself.

The author keeps this up. Olive vacillates between being awful and understandable and human and cruel, depending on the chapter. And, the way Strout does it, you don’t feel like it’s that the character isn’t well formed. As I said in my overview on the book, it seems like she’s known every character in the book for years.*

I’m reading the 2008 winner now, The Brief Wondrous Life of Oscar Wao. It’s happening here, too. Oscar and Lola’s mother, Beli, is pure evil in the second chapter. She’s abusive and manipulative in ways that turn your stomach. And when Lola understands she’ll never be perfect enough to make her mother’s abuse stop–and, besides, she doesn’t have the energy to try–the house gets dangerously hostile. Lola has to run. Junot Diaz, the author, has clearly made this character the villain of the book.

Just kidding! He doubles back on chapter two’s character work in the very next chapter. There, we meet Beli as a child, and we understand that she’s a broken little orphan, shattered by the world and with the same impulses we saw in her daughter in chapter two–the need to run. In fact, the author uses the unusual technique of calling her “our” Beli, burdening the reader with responsibility for who she becomes, forcing kinship with her in an insidious way.

When I think of what the authors are doing here, it could very easily backfire. The characters could appear inconsistent, confusing, ungraspable. But when handled right, this act of confounding themselves helps authors use each twist to turn the screw deeper into the wall, anchoring the character as an individual with complexities that reflect real humans. It’s a fascinating technique.


*Guys. Guys. I thought of the best pickup line for Elizabeth Strout. I forgot to put it in my overview post.

Setting: Bar
Me: Hey girl. Are you Zeus, because your characters spring from your head fully formed
Strout: ~Asks bartender for the check, excuses herself~

I’m not good at pickup lines, either.

Olive Kitteridge: Overview

Nothing like a two-week jaunt, especially with a few transatlantic flights thrown it, to give you the chance to catch up on some reading. I polished off three books on my beautiful trip to France, the first being Even Cowgirls Get the Blues (which I talk about here). The second book I polished off is part of my Pulitzer journey: Elizabeth Strout’s Olive Kitteridge, winner of the 2009 literature prize.

Coincidentally, a few days after finishing it, I saw that a show of the same name was taking the Emmys by storm. I had no idea they had made it into a show. Has anyone seen it? Opinions? (And what’s up with them making a show from A Visit From the Goon Squad? I’m over here tapping my foot, staring at my watch…)

Anyway, if they keep to the book at all, it’s bound to be a wonderful show. Olive Kitteridge was a sober, minimalist book, but don’t let that keep you away. It’s excellent in every way.

Tl;dr Synopsis


Speaking of A Visit From the Goon Squad, Olive Kitteridge is hybrid novel and series of short stories in which every chapter is tied to the last one via characters, without strict regard to chronology or continuity. But that’s really where similarities between the two Pulitzer winners end.

Olive Kitteridge takes place in a small Maine town, focusing on the residents there. It’s a beautiful book full of snapshots. Each chapter is a snippet of a life. You’ll encounter recurring characters in the chapters, especially Olive herself; she is involved in some way in nearly all of the stories. You’ll, in some ways, follow Olive from middle age to her twilight years and watch how she deals with the disappointments of everyday life. (Hint: with grizzle.) In other ways, you’ll just watch pieces of the townsfolks’ lives pass you by. You’ll be plopped in the middle of their story and in some ways be left to wonder how they got to where they were before you met them and what will happen to them later. That information usually never comes, but Strout manages to make this lack of information okay by resolving each chapter in a satisfying way.

Strout captures the essence of a rural small town perfectly. This seems like a book set oddly in the past, as if the town is still stuck in the thirties even as it’s clear that at least some of the book takes place post-9/11. When teenagers Tim and Nina storm on the scene with their phones and parties and modern vernacular, it seems as if they are aliens from the future come to throw the book completely out of whack, which is exactly how I imagine every person in the Maine town would feel about such people. These are simple folks who live simple lives, and the appropriately simple writing emphasizes that. Yet Strout still deals with the complexity of the human experience–depression, disappointment, humiliation, and even sometimes joy–without short-changing it in Olive Kitteridge.

Writing Style

Olive Kitteridge, as I said above, is quite somber. It takes a bare-minimalist, Hemingway-like approach to writing that really works for Strout. (Can I say, too, how many wonderful women writers they’re awarding Pulitzers to?) The author does a great job of showing and not telling. Melissa Bank from NPR says it well when she says, “The writing is so perfect you don’t even notice it…it’s less like reading a story than experiencing it firsthand.”

A short example is from one of the times we first meet Olive. A couple is over for dinner, and the very sweet, somewhat dopey, and rather abused Henry Kitteridge knocks something over at the table and Olive berates him in a way that makes you cringe for the houseguests. Strout knows she doesn’t have to say anything about how awkward anyone there felt. You can just feel it from the events alone, and there’s the added bonus of starting to see what it’s like to be around Olive.

I think one of the key examples of the simplicity of the story is later on, on the day of Olive’s son’s wedding. Olive has made herself a dress from scratch for the occasion–a bright print dress that she’s very pleased with. She looks at it several times with pride. Then, later, when she’s tired and goes to her son’s bedroom to lie down, she overhears her new daughter-in-law and other girls talking about how embarrassed for Olive they were that she could wear the dress in public. The author doesn’t do what many other authors might: talk about Olive’s anger or her self-loathing or sadness, or even something as subtle as heat rising to Olive’s face. Instead, the author stays fairly far out of the narrative other than to describe Olive’s delicious act of taking a permanent marker, finding one of the daughter-in-law’s cream sweaters near the bottom of a folded pile, and putting a bold mark across it, and folding it back into the pile. That’s pretty much all you get, and it’s more than enough.

Olive Kitteridge deals head-on with a lot of tragedy and loneliness, but it’s written in the least sentimental way possible. It lends the book a rawness and authenticity that’s striking. This is a book that stays with you, and it doesn’t use any cheap tactics to burrow its way into your heart.


The sheer number of characters you meet is rather daunting. Check the Wikipedia list. I count 94. You only hear about many of them once, though, and there isn’t a lot of pressure to remember them or confusion when they come back into the picture. It’s your own, personal little Easter egg if you remember, for instance, that the Daisy who nurses anorexic Nina is the same Daisy that Henry Kitteridge greats at church in the beginning of the novel. It’s a lot like how you can watch a random Law and Order episode and it really doesn’t matter much if you’ve been keeping up with the personal lives of the detectives. (Unless, of course, it’s SVU, which has devolved into a bit of a soap opera. Today’s blog post is turning into “Amanda’s Thoughts: T.V. Edition.” I’ll try to get back on track.)

The characters are all individuals. No one is going to be confused with the other, and you get the feeling that all 94 of these people are fully-formed individuals that the author has fleshed out before writing the novel. It’s amazing.

The characters are not necessarily likable. They waver back and forth. I changed my mind every chapter about how I felt about the Kitteridges. Sometimes I thought Henry was so sweet, sometimes I thought he was an absolute idiot, then I would feel bad about that and think he was sweet again. It’s really a lot how real relationships go, with a kind of ebb and flow to how you feel about the person as both of you grow and change and have interactions.   


You know, I found the first chapter to be a little jarring. There’s a serious feeling of being dropped out of a plane into the middle of a story, and you feel a little bit like someone may have torn out the first few pages of your book and you’re missing something. But looking back, I think the first chapter was my favorite. Olive sure isn’t cast in a good light in the beginning, but that first chapter is full of wonderful nostalgia and human connection and longing and remembrance. Oh, and you’ll learn more about Olive and feel for her later. The things she says in the beginning come from a place that you’ll understand, and you’ll be given the freedom to respect her, I think. See, I’m talking about these people like they’re real. They feel real.

Another highlight is all the chapters that portray people in love. Look for the chapter on Daisy and Harmon, for instance. There’s some sadness in it, but I mostly think it’s a beautifully hopeful chapter. There aren’t many of those, but the ones that exist are an experience akin to stuffing your face with Noodles & Co.’s mac and cheese. They feel indulgent and comforting. The book closes on that kind of note, and it’s pretty great.

Who Should Read this Book

I hate to say this because this book really is a masterpiece. But I don’t think it’s for everyone. It’s heavy. There are few moments of happiness in Olive Kitteridge, and the ones that exist are tinged with something undefinable that makes your heart ache. I think this is undercover one of the saddest books I’ve ever read. I say undercover because it isn’t like the reader’s constantly dealing with death after death after brutal heartbreak, etc. Olive Kitteridge mostly just deals with insidious disappointments that quietly accumulate day by day. When faced with it like this, in digestible book format, forced to acknowledge it over a few sittings, it’s hard not to feel like life itself isn’t something quite sad altogether.

So. If you’re a beach-reader who prefers lighthearted stuff and mainly uses books as a happy escape (no judgement here on that), this book might not be for you.

But if you’re okay with heavier stuff, it’s worth it to experience the craft of this book. The writing is executed in a way that stuns me. Strout does everything right. If I were teaching creative writing, which I am utterly unqualified to do, this book would be on my required reading list. It’s an example of writing at its best. And, despite the sadness, I really loved reading it. The book is gorgeous.

For What It’s Worth (A.K.A. My Opinion)

Wow, I think I already got it all out of my system.

If you can, you should at least try to read this. The writing stands in a category by itself, and the stories are gripping. It’s an experience that I think you should have, if it suits you.