20 Questions Inside The Primate Confessional

So, as I announced yesterday: CONFESSIONS OF A FREELANCE PENMONKEY is coming soon to a Kindle, Nook, PC or hallucinogenic dreamworld near you.

Thing is, in the spirit of the “confessional” vibe, I figured it might be cool to have you crazy kids ask some questions, and then I’ll answer the questions inside the book. A lurid, disturbed glimpse into the caffeine-sodden, booze-pickled mind of a freelance writer.

An interview! Of sorts. But with shame, pantslessness, and great gobs of profanity.

This is where you’re like, “Chuck, that’s a stupid idea,” and then I’m like, “If you don’t play along, I’m going to shoot this adorable baby penguin with a Taser.” And you’re like, “Whoa, that’s not cool,” and I’m like, “WHATEVS.” Then I drop your casserole dish. And it shatters. And the penguin bleats.

Do penguins bleat? I don’t goddamn know. Shut up.

So, if you’re interested in playing along (and you’d have my appreciation should you choose to do so), drop into the comments section and pop a question you’d like me to answer in the book. Obviously, it’s a writing-themed book, so one assumes you’ll ask a questions that at least flirt with the subject of writing, freelancing, storytelling, but hey, if you want to ask something entirely different, I’m not going to stop you.

I’ll select 20 questions out of the bunch to use in the book. Er, that’s assuming you ask me 20 questions. If you don’t, I’ll just make up questions, I guess. As I weep into my cereal. “Question number…”


“Number Seven. Why Doesn’t Anybody Like Me?”

*blow nose, eat Honey Nut Cheerios*

Right. Anyway.

Who’s in?

Questions go below. And thanks again.


  • If you could go back in time and give your newbie-writer self a piece of advice, what would it be? (Aside from “Don’t do that, get a job that gives you oodles of money and respect, what the fuck are you thinking.”)

  • As a freelance editor who helps make people’s work publishing-ready; my obvious self-plugging question is:

    Do you use an editor? Do you ulitlize someone else’s fresh eyes and valuable post-graduate-uni skills to improve your work? Or do you just write drunk, edit drunk, and rely on your own jaded and weary views of your work?

  • Just in case the previous comment came across as an insulting “you really need an editor”, it wasn’t meant to be. You are great! I was just pointing out to your many penmonkey readers the value-adding an editor can offer.

    End of plug.

  • What is the strangest thing you have ever written for publication or public consumption?

    A question not for the interview: have you ever read the introduction to All in the Timing by David Ives? Funniest interview answers I have ever read.

    And people do like you Wendig. We really do, I swear. No one payed me to say this, no matter what the shadowy figures tell you. Why else would I keep buying things you wrote and reading this blog? Also would those be Cheerios in milk, or rum?

  • What in the name of Gods is going to happen to us (next year?) when the Coffee Apocalypse hits and we can no longer afford to caffeinate? (Not an entirely frivolous question…)

  • Are there character or story ideas you habitually shy away from writing? Why? How do you feel that effects the quality of your writing?

    Yeah technically that’s three questions, sorry about that.

  • Is there any basic element of a story that you have issues with (i.e. the beginning or the end) and if so, how do you handle that?

    Obligatory: Where do you get your ideas from?

  • It’s trivial to write about someone stronger than you. It’s not hard to write about someone smarter than you. How do you write about someone wiser than you? How do you have a mentor dispense advice for the ages when you still can’t figure out that Irish car bombs for breakfast is a Bad Idea? How do you have an omniscient being reveal the truths of the universe when you have trouble unraveling the truths of Sesame Street?

  • How do you set and stick to a deadline without some outside agency (editor/publisher/etc) around to tap on a watch, make pointed remarks, or electrocute flightless birds?

  • In terms of drafts (first drafts, second drafts, re-drafts, etc) how many do you usually go through before you consider a work to be finished or fit for publishing? Corollary question: Do you think there’s such a thing as too many drafts, and if so, where would you draw the line on that?

  • A friend I don’t see very often was reading my book, and tripped and fell over the N word. I explained that it was the only word my racist (though they never saw themselves that way) parents would use. I even tried to correct them when I was in elementary school, and they became very angry. It was a word they had always used, and their friends had always used, and they were *not* going to change.

    I’m not sure everyone is brave enough to go where I went, but I just can’t falsify bad behavior.

    Should I have gone there, or just pretended everything was rosy?

  • How do you deal with the isolation of being a writer? How do you shut out opinions that might tell you to stop or give up or do things differently? It’s easy to say, “Do these things,” but harder to explain how they’re done. I’m asking you to explain how it’s done.

    • @Will: Dang, great question. So many answers contained in that one question.

      @Darlene: I assume you don’t mean “literally tripped.”

      Love all these questions.

      Keep ’em coming, you rocking humans, you.

      — c.

  • These are kind of more slanted to the “writing as a business” areana, but…

    Pen names: in a world where the internet can uncover almost any mystery, what’s the advantage to them? And if there’s no advantage, then why do people still use them?

    Marketing: Obviously, a publisher — if you sign up with one — will do some marketing for you, but it can’t stop there (and won’t start if you’re self-pubbing or have a smaller marketing budget). If you want to make writing your business, how do you…

    a) set about marketing yourself? It can’t be as easy as “sign up for Twitter”…
    b) balance marketing and business with getting the words on the paper?
    c) decide where to spend money to make money?

    And then, in regards to flat out writing:

    Do you have a routine that you fulfill before every project? i.e. draft character templates, burn them to ash, dance four times widdershins wearing the skin of an elk slain by your own hands, cast the ashes to the wind, have a drink of bourbon and sit down to write “chapter one”? Or do you wing each project?

    Muses: Aside from the fact that everyone but me seems to have one, do you believe in waiting for the muse to strike between projects or pages? Or is there a benefit to routine no matter how “inspired” you feel?

    …Okay, that’s all I can think of for now.

  • Why are you writing about writing?
    Will it be about the language, the art of telling a story, the bare bones compulsion to write daily?

  • What advice do you have for the kids (‘can’t legally drink/vote/DRIVE’ being the qualifier for ‘kid’) in the business who are trying to get shit done?

    Just an opinion question: Is it right for my mom to be getting on me how I’m not publishing anything WHEN I AM STILL A KID? WHO HASN’T EVEN PASSED HIGH SCHOOL?! Just want to see the new-parent aspect versus the been-there done-that opinion. Sorry about the angry teenager bit. I wrote for the school paper for a year, so I have published SOMETHING, if you count that.

    Do you have any advice for short story writers? All I ever see is stuff about novels and screenwriting. Do you think there is any market whatsoever for a compilation of short stories, or should I just submit stories to oodles of magazines?

  • Try as I might I just couldn’t come up with any awesome questions since it seemed like all of the awesome questions were already asked. The bit about the penguin was just awesome, though so I had to comment anyways.

    Actually wait…I have a couple of questions for you after all (feel free to answer or not answer as I asked more than one and they’re not 100% writing-related). What’s the best way to use social media to gain momentum about yourself? Is it important that you use social media at all? What is your view on cons and networking there (for those wanting to do stuff related to stuff that would normally be at cons)?

    -moar penguin bleating-

  • You’re an awesome story teller.

    Harry Chapin was an awesome story teller.

    Do you like Harry Chapin? If so, what’s your favorite song(s)?

  • What’s the closest you’ve ever come to killing another human? No, seriously. All of these writing-related question are great, and some should certainly be in the 20 you choose (probably *mostly*), but you need some bacos in this here salad. This is, after all, a confessional.

    Incidentally, if you have actually killed someone, that counts as “the closest you’ve ever come”. It’s not like The Price is Right, where it’s the closest $ guess without going over.

  • I’m curious about your thoughts on the topic of using proper English. My teachers in high school would be horrified, I’m sure, but it seems the tone of certain stories virtually requires a departure from the Strunk and White methodology we were all raised to write with.

    So with that in mind my succinct question would be, What is your stance on writer’s using the standard rules of English, exclusively?

    Your insight will be pithy, insightful, and limited to open-hand blows in the region of the face, I’m sure.

  • So many of your blog posts answer all the important writing questions — it’s really a challenge to think up any burning pressing issues you haven’t addressed. Well, at least those that don’t require a visit to a medical professional.

    Okay, maybe there are two not so burning or pressing questions:

    I’ve heard writers say that when thinking up an idea for a novel, before you start writing, you should make sure it’s “big enough” [heh] to support an entire book. It’s the kind of advice that makes you nod seriously in agreement and then later you wonder, Big enough? How the hell can you tell?

    Also, how do you decide whether to write a story in first person, third person, limited to what random strangers can see from the highest branch of the penmonkey tree person? I’ve heard writers say it’s merely personal choice and others who say you should write whichever is most uncomfortable to you — I know, like writing isn’t already hard enough, you should be uncomfortable. One of the Wendig-inspired flash fiction thingys I wrote was in first person and I realized afterward that it was the first piece of fiction I’d written in first person. It wasn’t a conscious choice; it just seemed to fit the genre (it was the baby pulp thing).

    I can’t think of any other writerly things. Though I am sort of wondering what kind of cereal you eat and whether you chose it because it stays crunchy even when drenched in tears — an important quality in cereal, whether you’re a writer or a teenage girl.

  • I’ve been wanting to ask you this for a while, actually, but the last time you had a Q&A day, you were sick and had lots of questions, so I thought I’d leave it for a bit.

    So, my question: I know you always say to finish what you start, which is good advice, but if you haven’t done that and you’re trying to do it before starting yet another new thing, how do you decide which project to work on? Are there criteria, like how much earning potential there is and where you can market it, or do you just work on whatever is most meaningful to you?

  • Over the course of growing as an author, do you ever feel stifled by your expected writing style? Do you ever want to evolve your style into something different, but feel you can’t because it’s your “author identity”?

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