Interview with Author’s Jilly Gagnon and Mike MacDonald

Choose your own Misery

Ian: How much does your past work at places like The Onion contribute to Choose Your Own Misery?

MM: I think The Onion has greatly informed the way I approach writing jokes. You can’t be too precious with your material and you have to work really hard to say something that isn’t cliched and obvious. It sounds counter-intuitive, but I think a lot of great comedy writing comes from writing around the joke, rather than always going for the jugular.

JG: I don’t think there’s a direct through-line from the Onion to this book; the style of humor is very different. That said, writing comedy is the best way to learn how to write comedy. Indirectly, all the years we collectively spent writing for other publications was the thing that made us ready to do this!

Ian: How much does your past work at more serious new establishments like Postmedia and Newsweek contribute to Choose Your Own Misery?

MM: Working at Postmedia, which happens to be the largest newspaper chain in Canada, inspired a lot of the misery found in the book. While we consume more news content than ever before, the economic model is completely antiquated. This means that I was working under the pressures of unrealistic deadlines, low pay, zero job security, and no foreseeable chance of upward mobility. It sucked pretty hard.

JG: Learning how to write a good engaging article for Newsweek was really instructive for comedy, surprisingly enough. You learn to cut out unnecessary filler (because you’ll lose your audience when that newsy article goes on for too long), and you hone your voice and style. To me, any writing you’re doing is important; it makes you a stronger writer across the board.

Ian: Do you still write for other publications?

MM: I’ll occasionally slap something up somewhere on the web. But after having wrote for various publication for the last five years or so, I’m trying my best to use that time to work on my own projects.

JG: Absolutely. I still write personal essays and magazine-journalism style pieces wherever they’ll have me. I also write young adult fiction–my young adult debut, #famous, comes out in 2017.

Ian: Congrats on the book, I look forward to it! 

Ian: Your book Choose Your Own Misery is a choose your own adventure format; what made you want to bring back this classic style?

MM: As a kid, I couldn’t get enough of those books. But as an adult, I find it hard to carve out time in my schedule to sit down and read a long piece of fiction. The idea of having a book which was interactive and conducive to reading in short spurts was really appealing.

JG: There were a few things at play. For writing jokes it’s a great format; the book is subdivided into all these little moments, and you have to make each one funny, which actually frees you up to get a lot crazier. If it were a novel with all these things happening to one character, it would seem like too much, but having a series of scenes the reader goes through, each of which feels almost like a standalone, allows you to get much weirder. We also felt like it was a style that was really well suited to modern attention spans; years of clickbait articles have trained us to love things in small, digestible packets. A choose-your-path book is perfect for that!

That, and we’re Millennials, so we’re basically obligated to love nostalgia for its own sake.

Ian: I myself am a weekend warrior, deteriorating and losing life forty hours; five days a week, am I the target audience?

MM: The target audience, in my opinion, is anyone who likes dark humour. While we certainly have a lot of jokes that hit on things related to the office, most of the humour comes from existential angst, loneliness, depression, etc.

JG: Absolutely! Anyone who’s ever been in a shitty job will probably relate to some of it, honestly. Though I hope no one can relate to all of it. That person would need a lot of help.


Ian: What gave you the idea behind Choose Your Own Misery?

MM: My friend told me about this video game where you have to drive from L.A. to Las Vegas, but in real time. If you successfully make it all the way there, you get one point. If you decide to spend the time driving all the way back, you get a second point. The concept sounded hilarious. From there, I thought it could be fun to write a book where a character is trying to get through a single day at the office. I told Jilly about the idea and she instantly came up with the titled Choose Your Own Misery. I knew we were on to something interesting.

JG: We have written together for ages, and we’re used to throwing out multiple ideas at once, knowing most of them would get rejected, and we’ll never pursue them (this is the dirty secret of comedy: almost everything you come up with is pretty terrible, then you occasionally come up with ONE not-terrible thing, and then you act like that’s the representative idea). One day Mike pitched this idea, and we both loved it right away. I think both of us working office jobs that were pretty terrible fits contributed to that Eureka! feeling.

Ian: I can imagine writing something like Choose Your Own Misery is very labour (Added the U for the Canadian, eh) intensive, can you describe the system you used for outlining and tracking the splits in the storyline?

JG: It’s super involved. We use this online flowchart building software, Gliffy, which has been a GODSEND. Before that, though, we were trying to mash the storylines into excel sheets, or storyboard them with post-its on the wall. That was a short-lived effort.

Now, we basically come up with a starting point, decide the two choices that could split off from that, and follow down a “line,” building in the additional choices as we go, until we get to the end. We throw that into the flowchart software, then start filling out the choice tree from the bottom up, going back to the next-to-last choice first (we figured out it’s the best way to not lose track of things, and to be able to map the storylines clearly). Once we’ve filled out everything for all the “dangling” choices from the bottom up, and we’re back at choice number one, we go in the opposite direction, build that line all the way to the bottom, and do it all again.

The planning takes WAY longer than the writing.

Ian: Are any of the characters based on real life people, maybe previous co-workers, or possibly a mash up of office types?

MM: We definitely have certain archetypes, like ‘the boss’ and ‘the love interest,’ and maybe a few of the people in the book are composite characters of different people we know, but we didn’t base any of our characters off of any one person.

JG: For my part, none of the characters were based on any one person; they were mainly archetypes you’d encounter at any office–the surly receptionist, the too-chummy boss, the strange coworker who’s WAY too friendly. Some of their particular mannerisms, though, or specific situations the character gets into, were absolutely based in fact.

And no, I won’t tell you which ones 😉

Ian: Is there ever a time that you just don’t feel funny and you hit the writers wall when it comes to comedy?

MM: We do our best to treat comedy writing as a job, so hitting a wall isn’t really an option. Or it’s as much of an option as not showing up for work. We’ll circle back to ideas and endlessly rewrite stuff, but we’re pretty good about getting stuff down on a page.

JG: Absolutely. All the time. Depending on how rough it is, we might try to keep coming up with ideas until something works, or we might say “this isn’t happening today, let’s focus on something else.” The good (and bad) thing about comedy is that it’s like any other writing job–there are plenty of things other than just writing the jokes that you need to be on top of–your website, book logistics, social media, not forgetting to feed the cats who are your only companions most days. Which makes you feel less worthless on days you can’t write a joke to save your life.

Ian: Other than each other do you have anyone that helps; maybe a significant other that approves of jokes, or in this case, approves of a choice in direction?

MM: We outsource almost all of our writing duties to child slaves in a factory somewhere in rural China.

JG: We’re the end-all be-all as far as both the specific jokes and the overall direction. Our agent, Dawn Frederick, is amazing, and her opinions always help us sharpen things up, and the editorial team at Diversion is also fantastic, but the two of us are the ones who decide whether we think something’s funny enough to write. Because at the end of the day, if someone else were feeding us the story, we might be able to write it out, but we almost certainly wouldn’t be able to make it as funny as if it came from our own twisted minds.

Part of the reason we work so well together is that we have similar taste in humor, but come at things from a slightly different angle (Mike’s a bit drier than me, I’m a bit weirder than him). Usually, between us, we have a strong sense of whether something’s working or not.

Ian: How valuable is it to be co-writers versus solo writers?

MM: I’m so incredibly fortunate to be able to work with Jilly. She’s easily the strongest writer I’ve ever come across, which I think is saying a lot seeing as though I’ve been lucky enough to work with some of the best comedy writing folks around. It’s sort of like asking Horace Grant how valuable it was to have Michael Jordan playing alongside him on the Chicago Bulls.

JG: In-valuable. I think with comedy especially, you need that other set of eyes–you can get too close to things and lose all perspective. If you perform comedy, the audience serves that purpose for you, but with written comedy, you usually don’t get that audience until a piece is in print, which is too late to fix it. Having Mike to bounce ideas off of–and to generate ideas I could never come up with–has been an incredible experience. I know for a fact that this book is much better than the book either of us would have written on our own.

Ian: Is there a downside to being co-writers?

JG: Obviously there are times when you disagree. Which can be very frustrating in the moment, but I actually think it’s a positive in the long run–if you have to fight for an idea, you have to really work out for yourself why it’s worth keeping…or realize that it isn’t, and suck it up. Of course Mike has to deal with me, so HE might see significant downsides.

MM: During the writing of this book I spent six months working in Tanzania and then six months working in Australia. The time differences, and in the case of Africa, the lack of modern infrastructure, made collaboration difficult. I’m sure it was super annoying for Jilly to hear that my “internet stick” was out of credit. But scheduling aside, I only see benefits in writing together.


Ian: You both have some background in TV, any plans on turning Choose Your Own Misery into something made for TV?

MM: In the book we have about 250 choices. It would be great to film each one and let the viewer decide how their television show will play out. The more I think about it, the more obvious it sounds. Hmmmmm…. I wonder if Alan Thicke would want to play the part of the boss?

JG: That would be amazing, and we both have ideas for how we could make this work. Know anybody at Netflix?

Ian: So what is next for Choose Your Own Misery? Is this something that will continue? Maybe Choose Your Own Misery: The Promotion?

JG: Actually, we have a second book already in the works–it’s tentatively titled “The Holiday Adventure,” and it’s coming out October 18! After that, there are plans for a third book, but we haven’t decided on the subject matter yet. I’m pushing hard for “the birth canal adventure.” It will be 100% period jokes that really dig into the nitty-gritty of uterus’s. LADIES IN COMEDY!

Ian: Are you guys working on any other projects that aren’t Choose Your Own Misery?

JG: We’re working together on a new project that we’re both really excited about, but it’s still early days, so I don’t want to spoiler anything. Besides that, I have the YA book, and another YA book in the works. And we both have the dream goal of learning taxidermy. Someday!

Ian: Where can people find Choose Your Own Misery?

JG: Bookstores everywhere–if they don’t have it at your favorite, ask them to order it for you! Or, if you’re impatient, you can buy it online–Amazon, B&N, Kobo, Target, and IndieBound are all good options!

Ian: Where can people get a hold of you?

MM: On Twitter and Facebook.
At Trinity Bellwoods park in Toronto, trying my best to make devil sticks look cool again.

JG: I’m on Twitter, on Facebook, and blogging/sharing news at!

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