25 Questions To Ask As You Write

Sometimes, as you write it helps to keep your eye on the ball, lest the ball thwack you across the bridge of the nose and make you cry in front of all your friends. Here, then — in time for NaNoWriMo if you’re going to be diving into that month-long novel-birthing experience — is a list of potential questions you can ask while writing your story in order to stay on target.

1. “What Is This About?”

This is, quite seriously, my most favoritest — and what I consider to be the most important — question for any author, writer, storyteller or general-class penmonkey to ask. Like I’ve said in the past, this isn’t just a recitation of plot. This is you going elbow-deep into the story’s most tenderest of orifices and seeing what lies at the heart of the animal. It’s you saying, “This is about how when people are stripped of civilization they turn into monsters, man,” or, “It’s about how the son always becomes the father,” or, “You dance with the unicorn, you get horn-fucked by the unicorn, you feel me?” It’s about identifying the theme of your work, about exposing the emotional core and the truth one finds there. You ask this question to make sure your daily word count lines up with your overall desire.

2. “Why The Fuck Am I Writing This?”

What I call: “The Give-A-Fuck Factor.” Why do you give a fuck? Do you? Why will anyone else care? Figure out what makes your story worth writing. Maybe it’s a character. Maybe it’s an idea. Maybe it’s one scene somewhere in the third act you just can’t wait to write. Find out why you’re writing this. If you’re just phoning it in, wandering aimlessly through the narrative without purpose, the audience is going to feel that. The audience can smell confusion the way that dogs can smell fear and hobos can smell a can of beans. They’re like sharks, those hobos. HOBO SHARK II: BLOOD BEANS III. I dunno. Shut up.

3. “Is This My Story Written My Way?”

When I read a story by Joe Lansdale, I say, “That’s a goddamn Joe Lansdale story.” The voice is his. The story is his. The characters are his. You could drag me to an alternate universe where Joe Lansdale was never born and still I’d know that this book in my hands is a book by him. We have to own our fiction. We have to crack our chests open with rib-spreaders and plop our viscera right onto the page. It’s gotta be us living there. Feel out the story. Feel if this is your story written your way (and if not, make it so). Write something that matters to you. If it feels like you’re not there? Backtrack, find out where you lost the story (or the story lost you) and rediscover your voice and your path.

4. “Am I Ready?”

You ask this before you start your project and before every day of writing: am I ready? Writer and El Sexorcisto Jason Arnopp said yet-another-smartypants thing the other day on the Twittertubes: “I’m seemingly destined to regularly forget that sometimes you’re not ready to write a script because you haven’t finished thinking about it.” Amen! So say we all. Sometimes you just haven’t done the brain-work. Or gotten all your plotting and scheming out of the way. It is our nature as impetuous creators to want to jump in and do a cannonball, but all that manages to do is make a mess. Sometimes, truth is, you’re just not ready.

5. “Does This Make Sense?”

Biggest problem with Hollywood big blockbuster movies these days is they don’t make a lick of goddamn sense. Seriously, I feel like I’m in one big game of Balderdash — I’m constantly asking, “Do they expect me to believe this shit? Did they dose up a four-year-old on Nyquil and let him write this plot?” You’ll find plotholes so big you could lose a Rancor Monster in there. Don’t be that way. When you’re writing, revisit the problem: does everything line up? Nobody’s just… pulling a gun out of their asshole or suddenly crossing 2,000 miles of desert in a day? Anticipate that your readers are going to be intelligent and will be able to smell mayhem and foolishness from a mile away. Have everything make sense.

6. “What’s My Plan?”

Have a plan and cast a wary eye toward it daily. It’s okay if your plan is: “I’m going to write until I’m done.” It’s fine if your plan is, “I’m going to write the dialogue now, then a few big action pieces, then I’m going to go back and fill in all the gaps.” Doesn’t matter what the plan is: it only matters that you’ve contributed a little brain-think toward it. Don’t be a pair of loose underwear caught on a tree branch.

7. “What Do These Characters Want?”

Characters have needs, wants, and fears. Simple as that. John wants a boat. Mary fears gonorrhea. Booboo the Space Whale needs to eat a supernova-ing star or he’ll die. Every character is motivated, and that motivation is the engine that pushes them from one end of the scene and out the other. Asking this while writing helps you keep the motivations of these characters in line: these motivations drive the plot.

8. “What’s The Conflict?”

Every character has a motivation, and then you come along, the Big Ol’ Grumpy Dickhead Storyteller and throw all kinds of shit in their way to stop them from realizing their hopes and force them to confront their fears. This is conflict. Hiram wants to have a dance party at the country club but OH NOES he just got kicked out of the country club because his rival, Gunther, has been spreading lies about how Hiram likes to “lay with caribou.” Now Hiram must defeat the machinations of his rival and prove his worth to the country club. What Hiram wants is prevented by conflict. So, every day, identify the conflict. Not just in the overall story but in each scene. How do the little conflicts build to larger ones?

9. “What’s The Purpose Of This Scene?”

Every scene has its purpose. Find it. Expose it. In this scene, you need to show Rodrigo’s helplessness. In that scene, you must foreshadow the showdown between Orange Julius (Secret Agent: Orangutan) and his foe, Hobo Shark. The scene after will see the protagonist lose everything and drive home the overwhelming difficulty. Blah blah blah, etc. As you’re writing, find the purpose. Let it impel the day’s writing.

10. “What Has To Happen?”

Every plot is like a machine. Some are simple — a lever, a pulley, a nut-cracker. Others are far more complex. No matter what the case, every machine would fall apart and fail to function without certain key components, and your plot is like that. These are the legs of the chair: you need them or the story will fall over and break its teeth on the linoleum. Keep your eye on these. Know when you’re approaching one. Orchestrate them. Find the way to each. Make the No Man’s Land between them compelling, too.

11. “How Does The Setting Affect My Story?”

Setting matters. (Someday soon I’ll do a “list of 25″ about setting.) Setting contributes to conflict (snowy blizzard!), to interesting characters (Brooklyn hipster!), to mood (a low rumble of thunder indicating slow-approaching doom!). A great setting puts a great deal of story toys on the table. You’d be a fool not to grab a couple, put them into play.

12. “What Do I Want The Reader To Feel?”

The storyteller is a puppetmaster. You’re here to pull strings and make people feel something — often intensely, often deeply. And so it behooves you to aim for a feeling rather than randomly hoping one occurs. In this scene you’re writing, what do you want the audience to feel? Hopelessness? Triumph? Delight? Fear? Do you want them to laugh so hard they get a nosebleed? Or cry until they fall into a grief-struck slumber?

13. “Am I Enjoying This?”

Not every day is going to be a thrill-a-minute. Some days the word count is bliss; other days it’s like brushing the teeth of a meth-cranked baboon. But you should keep an eye on your overall enjoyment levels. You should be finding some pleasure, some measure of satisfaction, with what you’re writing. If not, try to suss out the reason. If you find it a misery, there’s a chance the reader will feel that misery, too.

14. “Am I Taunted By An Endless Parade Of Distractions?”

As you write, it’s best to ask: oh, shit, am I actually writing? Because, as it turns out, being on Twitter doesn’t count. Nor does playing a video game. Or watching football. Or cranking one out to obscure Prohibition-era pornography. We writers are easily distracted, like raccoons, babies, and — I’m sorry, where was I? The sun just glinted on a quarter and I found myself mesmerized for — *checks watch* — about 45 minutes. Point is, if you’re easily distracted, you need to cut that shit out. If it continues, you need to find out why. Why is it you don’t want to write the thing you (theoretically) want to write?

15. “What Else Is In My Way?”

We all find our work hindered by various reasons. Family obligations, writer’s block, technical problems, depression, vibrant hallucinations, addictions to huffing printer ink, etc. Time to identify these reasons — and by reasons, I mean, “excuses” — and begin systematically eradicating them. Find what blocks you, and either remove the block or find a way around.

16. “Where Are My Pants?”

Trick question! You should know where your pants are. They should be as far away from you as possible. Good penmonkeys work pantsless. I, for instance, pull a “Garfield” and mail my pants to Abu Dhabi.

17. “Am I Writing To Spec?”

If you’re rocking the NaNoWriMo, you know your count is 50,000 words. Or maybe you’re writing a 90-page script, or a 5,000-word short story. Always keep your mind roughly orbiting your total potential word count: good writers know to write to spec and, in the day-to-day act of penmonkeying around, recognize when they’re on-target or off-base.

18. “What’s My Daily Word Count?”

Part of writing to spec is knowing what your daily word count should be. If you’re writing NaNoWriMo, it should be somewhere between 1500-2000 words per day. Hit the target. Bing bing bing bing bang, popcorn.

19. “Who Is My Audience?”

This can be as broad or as limited as you care to make it. Your audience might be, “Everybody who loves a good thriller” down to “Teen boys between the ages of 15-18 who still wet the bed.” Just as good authors write to spec, good authors also write to an audience. A speaker would tailor his speech to his audience, and so the writer must tailor his writing to an audience as well.

20. “Have I Saved Recently?”

I am an obsessive-compulsive saver. I will save at the end of every sentence if you give me a chance. I’ve probably saved this blog post 1745 times — 1746 now! — over the course of its writing. Seriously: save a whole lot. Learn to ask yourself that question in order to keep it and the habit top-of-mind. Oh, and just so we’re clear: don’t rely only on auto-save. We cannot trust robots with our future. Because robots hate us mewling meat-bags and secretly work to undermine our so-called “agenda of the flesh.”

21. “Oh Shit, Do I Have This Backed Up In 72 Different Places?”

You must save often and back up your work across multiple sources. External HD? Cloud storage? E-mail yourself the draft? Print copy? ALL OF THE ABOVE, TYPED IN CAPS TO DRIVE HOME ITS SCREAMING IMPORTANCE. RAAAAR YELLING YELLING SNARRGH. Ahem. Point being, at the end of every day’s worth of word-making, back up the file in as many ways and places as you care to manage. Future You, upon suffering a cataclysmic hard drive shitsplosion, will thank Present You for being so damn smart.

22. “What Will I Write Tomorrow?”

Toward the end of this day’s word count, keep an eye on tomorrow’s story-telling endeavors. Maybe make a few in-document notes. Keep a hazy picture of what happens when you next sit down to write. You’ll be happy when tomorrow comes. Unless tomorrow doesn’t come and the robots have finally decided to wipe us from the planet like one might wipe a booger off a drinking glass. Fuckin’ robots, man. Fuckin’ robots.

23. “Does This Look Like Shit?”

Does today’s word count look like garbage? Spelling errors? Funky plotting? Hastily-scrawled poop? That’s okay. You’re allowed to do that. Just note it. Make a little checkmark in your brain, or even do a comment in the document — just know that today’s word count will necessitate you coming back, doing some clean-up.

24. “Is This A Good Day To Write?”

Trick question! Every day is a good day to write. Go and do that which you claim to be. Writers: write.

25. “Am I Asking Myself Too Many Goddamn Questions?”

Of course you are. This post posits too many questions to seriously ask yourself: the point isn’t to compulsively go through this list of questions day in and day out, but more to help take these questions and let them float in the back of your mind: if you grow too crazy about this, you’re going to be focused more on the answers than you are on your actual word count, and that’s not the point, not the point at all. These questions are — well, you know what they’re like? You know how when you drive on one of those go-cart tracks they have the haybales up or the rubber bumpers to stop you from careening off-track and to your fiery doom? These are like that. These questions are what help keep your go-cart from flinging off into infinite space. Let them shepherd your word count rather than overwhelm it. Don’t blow a gasket. Use them where they’re useful; discard them with they’re starting to fritz your circuitry.

* * *

Want another booze-soaked, profanity-laden shotgun blast of dubious writing advice?

Try: CONFESSIONS OF A FREELANCE PENMONKEY

$4.99 at Amazon (US), Amazon (UK), B&N, PDF

Or its sequel: REVENGE OF THE PENMONKEY

$2.99 at Amazon (US), Amazon (UK), B&N, PDF

And: 250 THINGS YOU SHOULD KNOW ABOUT WRITING

$0.99 at Amazon (US), Amazon (UK), B&N, PDF

31 comments

  • Love the questions. Especially the part about writing for the audience. I’ve been struggling with this, because I feel that writing for audience mutes the creative voice of the writer. For example, i really want to write a horror story full of blood, guts and general mayhem but the audience I know, they want a love story full of romance, sighs, hearts and candies. Yeah, so it’s a struggle, but I am working my way through it, one word at a time.

    thanks for writing, man :)

  • Well, gee, Wendig. Thanks for claiming the main plot twist of my novel BUTT PLUG MAGNUM* makes no sense.

    You’ll be hearing from my lawyer. (And by “lawyer”, I mean the H&R Block guy I call every time I end up in the tank for DUI.)

    *It’s noir. Very noir.

  • Riffing off #5: When something doesn’t make sense, I like to see it as an opportunity rather than a problem. People in writing groups often say things like, “He *has* to cross the desert in two days because he has to be in a particular place at a particular time for the plot to work the way I need it to”. It’s even worse when the character starts doing out-of-character things to serve the mechanical god of plot.

    I like to ask, “So what happens if he *doesn’t* get where he’s supposed to be in two days?” Does all hell break loose? Is that really a bad thing? If two characters *need* to come together, isn’t it more interesting if everything in the universe tries to thwart them? Isn’t your job as a writer to put that character through hell? Sure, crossing a desert is bad, but there’s *always* a way to make it worse.

  • First time here, lured by a tweet – great advice to yet another aspiring penmonkey contemplating the NaNoWriMo monster (though I don’t buy the pantsless situation. I’m guessing that’s a gender thing. Or else a whole symbolic, philosophical thing that went way over my head.) The baboon sentence totally made my quote collection.

  • Awesome article. I admit that over the years I’ve gone from hiding from these articles to loving them. I agree with all but the pants thing. That said, I’m English so I can take that as cause to go commando in the flat.

  • Number 14 reminds me I have a clever idea I was hoping you’d write out in a clever vulgar way (we can split the profits).

    Turns out the DVR is a great way to make a football game last an hour; then I can spend the other three feeling guilt for not writing.

  • My questions/thoughts while writing:
    Should I really have opened that second bottle?
    Oprah seems like a cunt, I wonder if she is?
    Maybe I should open another bottle…
    My chair spins, sweet.
    How did I end up on PerezHilton.com?
    I wonder what Chuck Wendig is wearing?
    Four paragraphs on my love of boxed wines isn’t great…it’s AMAZING!
    *passes out on keyboard*

  • OMG #20 YES.

    Our backup server took a flaming shit a week or so ago. ALL my work was backed up there, in keeping with the good little overly-complacent-failure-to-backup-properly-in-at-least-THREE-locations I used to be. We’re waiting for a recovery service to get back to us with an evaluation and a quote, and I’m about out of Ativan. Fuck fuckity fuckaroonie fuckedadoodledoofuck. Fucking embrace the fuck outta multiple redundancies when it comes to backing up your work.

  • Certainly closer to #3 than ever before, but I’m not sure if I’ll ever know this unless someone tells me.

    Brain-work for #4 and #6, very important. Some of my best writing doesn’t involve writing. Thinking, talking to people, doing stuff.

    But I do suffer from #14.

    Carry out #21 religiously.

  • Did anyone else spend twnety minutes puzzling over that damn picture at the top before finally clicking it to figure out what the hell it was (fastball stitches) and then feel guilty when reading the “remove distractions” section?

  • Go-karts flinging off into infinite-space? Sounds like an intense track you race at.
    I thank you for your hay bales and tires and rubber bumpers you set up in this post, very helpful.

  • Yeah, I know, it’s the 25th already but I do read your posts eventually, Chuck. This one is tagging along with me today as I head to the white noise of my local mall to plot and plan this year’s NaNoWriMo project. Your 25 tips will act as a guide . . . or a distraction in case my Muse heads off to the food court, leaving me with my half-drunk, cold coffee and a hunkering to follow Her.

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