Episode 8—Maggie Messitt on Shi#y First Drafts and Making Documentaries on Paper

maggie messitt, the rainy season

Written by Brendan O’Meara

Tweetables by Maggie Messitt (@maggiemessitt):

“I really embrace the shitty first draft.” 

“I was always into true stories, almost at an obsessive level.” 

Maggie Messitt wrote a gem of a book in The Rainy Season: Three Lives in the New South Africa. 

We talk about a lot of stuff, certainly about process and the challenge of writing book-length narrative. Maggie is a writer, author, teacher, hiker, dog owner, reporter, super kayaker, all-round liver-of-life. 

Also I introduce a new segment called the Bookshelf for the Apocalypse. What’s this? Should the world be ravaged by global pandemic, zombies, meteor strike or nuclear winter, and you were allowed ten books to keep in your survival pack, what would they be?


Below you’ll find a list of books Maggie mentioned that you may want to check out. Thanks for listening and I ask that you please subscribe to the podcast and sign up for the email newsletter.

Thanks so much!

Maggie’s Bookshelf for the Apocalypse

The House on Mango Street by Sandra Cisneros

The Spirit Catches You and You Fall Down by Anne Fadimann

Pilgrim at Tinker Creek, An American Childhood, A Writing Life, all by Annie Dillard

Notes from No Man’s Land by Eula Biss

The Faraway Nearby by Rebecca Solnit

Open City by Teju Cole

Portrait with Keys by Ivan Vladislavic

A dictionary

What is Justice? by Robert C. Solomon and Mark C. Murphy

Make a List of Validations, Not Rejections

When suiting up, never forget to accessorize.

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By Brendan O’Meara

I’m sure you’ve heard the famous Stephen King quote about his rejection slips. The one where he said he used to hang them up by a nail, but then he needed a spike. Let’s let him say it (h/t Alex Strike):

By the time I was fourteen the nail in my wall would no longer support the weight of the rejection slips impaled upon it. I replaced the nail with a spike and went on writing.

That’s a nice image of writing in the face rejection, but who needs to see all those rejection slips? Some people are motivated by them. It’s what athletes do. When someone like Tom Brady, a winner of four Super Bowls, was drafted 199th overall, he used that as motivation. That was like receiving 198 rejections over the course of a weekend.

[Hey, if you’ve made this far, please sign up for my email list. If I post on the blog, it goes out once a week. If you sign up, you’ll be on the frontline for goodies. Thanks!]

Sometimes, though, you see those rejections and you start to believe them. You start to see them as a way out. Maybe you’re deluding yourself in whatever art you choose. The rejections are like a virus that must be purged.

I used to keep rejections. I used to like to see them pile up, but then this began to poison my thinking. If they don’t offer anything constructive, which almost none of them do, I delete them. Instead, I keep a list of validations.

These are so powerful. These are Exhibit A in of You v. Delusions, that you should KEEP GOING.

Keep a file of praise from readers (the most important, because they, you know, buy your work),  mentors (almost as important) and family/friends (don’t let this be your only validation).

It’s not stroking your ego. It’s keeping your soul alive in the dark moments when you want to quit, when you’re looking for every ounce of permission to get out of the game, when you’re looking for one person to tell you to stop deluding yourself.

There’s a fine line between a life in the arts and the delusional. Validations are tangible reasons why you keep going and keep trying to push through.

When Backstory Feels ‘Deliberate’

Day 4: about 20% through the book. Will it be worth keeping? Should it be chucked? We’ll see. #writing

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By Brendan O’Meara

In yet another bout of mapping vs. outlining (mapping is just reverse outlining. The terrain of the book is in place and you set out like Magellan and map the world. Very clever, I know.) I’m hitting the notecards pretty hard. See pic.

I’m at this point in the this book where I just backed up the dump truck and unloaded a chapter of backstory about my central character. Reading it feels laborious. I haven’t touched this manuscript in four years.

I’m thinking of gutting the entire backstory thus leaving my main guy a little mysterious, a little cloudy around the edges, like Gatsby. He is my Gatsby and I’m Nick, an unreliable insider-outsider who greatly admires his Gatsby.

I love seeing giant limbs of text come tumbling down. I prefer the chainsaw to the pruning sheers.

In Maureen Corrigan’s great book So We Read On: How The Great Gatsby Came to Be and Why It Endures, she meets with Scott Shepherd toward the end. Shepherd reads the entire novel once a day for the broadway production Gatz. He actually has the text memorized. That’s not hyperbole.

Corrigan speaks with Shepherd about Gatsby’s (the character) backstory. Shepherd says of the four-and-a-half-page section that fills in Gatsby’s early backstory:

The beginning of chapter six was sometimes tough. That’s when the audience [for Gatz] would just be back from the dinner break and the’d be logy with food. There’s something about that section that feels deliberate.

Max Perkins, the famous editor to Fitzgerald and others, pushed for Fitzgerald for more biography. Shepherd continues:

In my mind, I see Fitzgerald inventing more specifics in the backstory because Perkins told him to, while at the same time dealing with his strong impulse to leave most of the questions unanswered. The result is, to my ear, a slightly obligatory and vaguely evasive quality that’s artificial in comparison to the rest of the book.


In nonfiction (and all writing for that matter), there’s this tendency to fill backstory, backstory, backstory to round out the character. It’s how most reporters write a 1,000-word take out. It’s basically ALL backstory with some quotes. These past events are why you care about this story about me today.

When we’re dealing with narrative, every word is an oar that must row the boat forward. If you’re going to pause for backstory, that backstory needs to inform the foreground. If we’re going to tell you something that happened way back when, there needs to be some sort of payoff or at least a connection to the foreground.

In my mapping of this first book I wrote, I find this backstory chunk merely background with very little of real substance. Of the 5,000-8,000 words, I bet there’s a 1,000 words worth keeping to pepper throughout the rest of the story.

It feels, to echo the above statement, deliberate. Deliberate feels labored and, worst of all, boring.

Yes, we need to know where our characters came from to have a better understanding of why we care about where they’re going. But too much and we’re too anchored to the past and all forward momentum is lost.

Hey, folks, if you made this far, I’d love your email address. I send out a weekly newsletter with the week’s posts every Tuesday morning. Also, for your loyalty and permission, whenever I have freebies you’ll be the first to know. If I’m selling a book, I’ll make sure you get a discount somehow. You’ve given me your time. I give you story, and maybe a few extra dollars in your pocket. Thanks! 



The Age of Process or The Story Behind the Story as More Important Than the Story

Fatigued pencil. #keepwriting

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By Brendan O’Meara

Listening to the run up to the Oscars, what was the main thing you heard about Richard Linklater’s Boyhood? It wasn’t how great a movie it was or how powerful the performances were. It was This movie took twelve years to make!

The marketing machine behind this movie was brilliant. I haven’t seen Boyhood yet (I will), but the true brilliance of this movie is the story behind the story. The actors and filmmakers committed a few months every year for twelve years to make the film.

This story behind the story was more powerful than the story itself.

So what’s the lesson? As I see it, make your process as transparent as possible and make the making of your art part of the narrative. Blogs are perfect for this. Show Your Work, as Austin Kleon would say.

Part of Boyhood’s appeal was this notion of backstory. Whether it was intentional or not from the outset is unknown, but once it became part of the movie’s machinery, it was this unbelievable talking point that made the movie irresistible to viewers because people kept saying, “Can you believe this movie took twelve years to make?”

This backstory was even more powerful than the actual movie. A Google search for “boyhood took 12 years to make” yields over 4 million hits.

Blog about your book. Take pictures. Make little confession movies. Make a mini documentary about your project. Pretend someone is interviewing you and answer questions. Create a story about the story and people will read the story you want to sell.