Writing With Friends: How It Works -The Toast

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Home: The Toast

Jilly and Mike’s book comes out today, and you can buy it here. Or elsewhere, but if you buy it here, we would get some money. I find collaborative writing fascinating, and if you do too, check out the piece the Fug Girls did for us on this topic.

People—okay, maybe just I—have all kinds of romantic visions of what it means to be a writer.

There’s the “furiously typing as daylight fades, then stars come out, then the sun rises, at which point you dazedly realize you’ve been geniusing all night” montage.

And of course the “storming around the unheated garret, hands wreathed through your hair, as you battle the demon that is your muse” trope.

And who could forget the thing I actually do: “talking to your cats significantly more, percentage-of-speech-wise, than you do to human beings.”

They’re all wrong of course (except the cat one) but there’s a kernel of truth to most romanticized ideas of the writer:

She’s alone.

Always alone.

The idea of writing being a solitary endeavor is deeply ingrained, and it’s appealing from a distance, the way being an orphan seemed appealing when you were nine—somehow the aloneness is proof that you’re special, different, destined for this in a way attorneys can only dream of.

It’s also the way most of us come to love writing and reading: hours spent under blankets with flashlights, scribbling in a journal you gave a human name to, because you read The Diary of Anne Frank and thought that was de rigueur. By the time you start writing seriously, the solitude comes naturally.

It wasn’t exactly simple to wrap my head around writing with a partner. And yet my debut comic novel, Choose Your Own Misery: The Office Adventure, was totally collaborative (with my co-author, Mike MacDonald) from the outset.

Having written two books together now, and countless other “never went anywhere” projects, it’s an experience I’d recommend to everyone.



You need a thick skin to write. Rejection from agents, editors, critics, and the comment section (stay away from the comments, for GOD’S SAKE!) are napalm on your self-esteem.

Writing with someone else is like nuking the ground you previously napalmed. Then salting the earth. You’ll not only destroy both your egos, they’ll only ever grow back with flippers.

The idea we settled on for CYOM: TOA—an extremely dark-comedy choose-your-path novel in which things start terribly, then get worse—was one of three that Mike tossed my way one day in February of 2013. 

I told him the other two books I wouldn’t want to read. Ever.

None of my ideas made the cut at all.

That’s the entirety of the CYOM origin story, and it was just the first of many hundreds—actually, probably thousands—of micro-rejections we’ve given one another while writing it. 

Because it was a choose-your-path story, the first stage was intensive planning—choosing a starting point, then which decisions you’d be given, then where those might lead next, then, then, then.

We have multiple email chains that run into hundreds of messages:

screenshot_01 CYOM node

screenshot_03 CYOM nodes

screenshot_04 CYOM nodes

There were another 80+ emails after that.

And that was just one part of one string. The book literally has dozens of strings.

Coming up with ideas was less than half of the process of planning the book.

Abandoning them—quickly, willingly, without getting butt-hurt—was much more important. If there was something one of us really loved, we’d fight for it. More often, though, we’d simply let the idea go. You learn quickly when you’re working with someone that it’s ultimately less painful not to be married to much of anything you come in with. Often the thing you’re most excited about falls flat for the other person. Just as often the thing you assumed was a throwaway—lazy work you barely squeezed out at the end—shines.

The whole point of having this other person in the room is valuing their opinions, and trusting that you’re both after the same goal: in our case, the funniest fucking book we could write.

You don’t get there by only liking your own ideas. And you certainly don’t get there by getting upset by every “meuh.”

Besides, once you get past the sting, you realize something amazing: those “meuhs” are forcing you to come up with stuff that you know—deep in your gut know—is better than what you had before. Weirder, loopier, more biting—“meuh” really just means “we can do better.”

When I write on my own, I only make it as far as a good-ish idea (occasionally). Goodish I’ll write. Having someone tell you flat-out “but it’s not great” allows you to get to…well, better.

The other benefit? The rest of your writing life starts to hurt less. Pitching Mike a joke I think is killer and getting a “meuh” sucks…but it happens dozens of times every week. Having a full-on depressive fit is not only insane, at some point it’s emotionally impossible; you’re too desensitized to “meuh.” 

…which makes it easier to take the next-level rejections. The ones from the agent you knew would be into this, or the only publisher you could ever imagine the book with, or the outlet you need a review from.

You actually start to internalize that clichéd cold comfort: “no” sucks, but it’s almost never personal, and it’s certainly not the end of the line.

You also have a built-in release valve for the “my mother was right, I should have gone to law school” days.

Other writers will nod sympathetically when you tell them about a rejection, but they don’t actually want to help you analyze the exact wording of the email for a fourteenth time. Not because they don’t care, but because they’re also doing the same thing all the damn time.

Your writing partner? Usually hung up on the exact same things you are. Which means you can catharsis all over each other whenever you need it.


There are plenty more “why”s to writing with someone else—meetings are a reason to put on pants! And get up before noon!—but there’s also the “how.” Writing is usually a solo endeavor; how, exactly, do you share that process? 

Thank everything for the internet.

For Mike and I, collaboration often took place across continents (Mike was working in Africa, then Australia, during much of the planning of the first book). We bounced ideas back and forth in emails, shared google docs and sheets, and started plotting what we’d come up with on a flowchart-mapping service, Gliffy, without which we probably would have given up on the whole thing.


This thing took awhile.

Most of all, we talked (usually via Skype). There’s no single tool that’s more effective in creating a good co-written product than face-to-face conversation. Your ideas grow one another, you actually see the huge laugh or not-quite-hidden grimace, and you save a HELL of a lot of time.

After all that is done: write alone.

You could try to write as a team in real time—we’ve done it for short pieces before—but usually that just winds up being solo writing with a constructive audience for one partner or the other.

So we’d set ourselves deadlines—you tend to keep them when you’re not the person you’re letting down—write alone, then edit as a team, reading our section aloud to the other person before diving in to “fix” it.

If you can’t write with a partner, just do that part: read your work aloud. You’ve heard it before, but it works. Suddenly you hear yourself speeding up to get yourself past a too-long, boring bit. Using the same word a million times is impossible to ignore. And if, like us, you’re writing comedy, you get to hear the rhythm of the joke. Believe me, it matters. A lot. 

*Fart noise.*  see?

I know, deep in my gut (which is much, much more sensitive than my heart), that Mike’s and my book is infinitely better than the book either of us would have written alone. Making each other laugh wasn’t just motivation, it was proof of concept. Hearing ideas that you’d never consider, because they’d never come out of your own head, took it in directions we’d never have found separately.

Most of all, having a built-in support system all the time helped ward off the despair that is almost unavoidable when you’re writing. The best argument for collaborating on something—whether it’s a three minute YouTube sketch or an intense, only-sorrow issues-novel—is getting that close to another writer, knowing there’s someone out there who wants your success as much as you do.

That last bit was pretty cheesy.

If Mike were writing this with me, he’d know whether to edit it out.

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