Balls of Steel: Penmonkey Darwinism

When I first started screenwriting, I was immediately whipped with a wet blanket of advice: “It’s easier to sell a novel than a screenplay.” Incredulous, I did some research, and it didn’t take long to conclude that advice was dead on.

Uh oh. There goes plan A.

My favorite mysterious guru, Unknown Screenwriter, wrote a post last week about the odds being against us. I suspect the reason his words shocked and irritated new writers was because he shared what they didn’t want to hear. He provided stats showing one spec screenplay sells for every 5,000 that are written.

Survival of the fittest.

It’s not about brawn; it’s about brains. You need to be crafty, swing from the branches, beat your chest, and eat bugs off the dead you leave in your wake. While everyone is running in the same direction, maybe you need to go the opposite way and machete a new, less-traveled path.

Being a ballsy, practical girl, I needed to reevaluate my definition of being a “writer.” What better way than to find a role model.

Meet penmonkey, Chuck Wendig — fearless writer of everything and anything his crazy brain can come up with.

I first met Wendig on Twitter, watching him banter with the spar-worthy literary agent Colleen Lindsay. I quickly fell in love with his 140-character dry humor. His writing voice is unique, intelligent, and yes, sometimes profane. But he keeps it real. I respect that.

Within 10 minutes I was perusing his website, Terribleminds, wanting more. And more I got. Holy wordsmithers, Batman, this penmonkey is a freelancer on steroids.

Wendig lives the life of a writer on the edge of insanity, writing articles, novels, short stories, game design, blog posts … and screenplays. By the way, since that first day of stalking Wendig, his site has been named one of Writer’s Digest 101 Best Sites for writers.

As I soaked in Wendig’s long list of accomplishments, his strategy became crystal clear — a writer writes.

I’m of the same multitasking mindset, in that my label is “writer of things.” My goal is to be a paid writer, not just a screenwriter, hoping one of my many angles would eventually help me get a script sold and produced. But Wendig pushes the envelope even further than I dare.

I had to know more about the man behind the penmonkey label.

Wendig started his professional writing career at the age of 18, with his first published short story. Now a full-time writer, he has built an arsenal of published work, but always seeks the next challenge.

Enter screenwriting.

He found the Stephen Susco Screenwriting Competition, but had no script to submit. Since his book Blackbirds hadn’t been sold yet, he started adapting it as a screenplay and submitted a portion to the contest.

He won.

With that, he also won Stephen Susco as a mentor for an entire year. Yes, that Susco — screenwriter of Grudge, Grudge 2, Red, and more.

Having written both novels and screenplays, I was curious how he felt the forms compared.

The writing stage of screenwriting is fast, while the editing part is not. But there’s something lean and mean about a screenplay. It allows you to focus deeply on story instead of prose. Novels are a game of inches.”

Regarding the overall results of both forms, Wendig clearly feels a difference.

The screenplay is not the end result. The novel is. With a screenplay I find a lighter stress factor because you’re creating a template, a blueprint. It’s easier to take your ego out of it. The novel is all yours. That white whale you hunt alone.”

In that blessed year with Susco, Wendig worked on Blackbirds and another script based on one of his short stories. When the year was up, Susco introduced him to Lance Weiler, writer and director of Head Trauma, who was in search of a partner.

After Wendig picked up Weiler in a seedy bar … oh wait, that was supposed to be off the record. Never mind that. The team of Weiler and Wendig has been together for over five years. That’s a lot longer than most pick-ups. Bravo, gentlemen!

Remember that 2010 Sundance Screenwriter Lab I never got to go to with Slavery by Another Name? Well, Weiler and Wendig were there with their script, HiM.

Excuse me while I sit in the corner and lick my wounds.

But at the risk of sounding like a gushing fan, to lose to this caliber of writer is an honor. I truly am in awe of Wendig’s work.

Wendig shared how incredible the Lab was. “As a freelancer everything is so focused on business. How much could I make for this? Is it worth my time? But at the Lab, it was about craft and story. About the deeper, weirder shit that goes on in a screenplay — the compressing of story. We had the time to explode that out and find the details that weren’t working.”

Sounds like writer Heaven.

But once back in his “Pennsyltucky” home, as he calls it, Wendig dove back into reality and focused on all his other projects, including two new self-published e-books, Confessions of a Freelance Penmonkey and 250 Things You Should Know About Writing. The first serendipitously launched on the day his son was born, just eight weeks ago.

Why a published author would choose to self publish is a complicated discussion, but Wendig believes both traditional and self-publishing are necessary, because at this stage, there’s no way to predict which format will be the survivor. Simple Darwinism.

To widen his net even further, Wendig has written spec TV scripts.

You have to know what network you want it on, and how many acts that network uses. In film scripts you have three acts (or four, if you like to break the second act in twain), but with TV there are mini acts where you have to keep the audience hinged for the commercial break. Writing TV is in some ways trickier, more slippery. A different expression of story demands a different approach.”

Wendig’s list of accomplishments impresses the hell out of me. But what impresses me most is how he took an opportunity of a single screenwriting competition and turned it into an entirely new career. Sure, he had Susco’s attention for a year, but Susco would never have recommended Wendig if he hadn’t done the hard work to earn that introduction.

He was smart. It’s how you survive in this business.

I asked Wendig what he wished he could tell his 18-year-old self.

When I write my blog posts, I’m yelling at the 18-year-old me, combating the bullshit I believed all those years ago. Regarding the industry, I’d tell him there’s not a specific path. Everyone comes at this career from a different angle. We all dig our own way in and detonate it behind us. It’s important to know you can survive as a screenwriter by doing it your own way.”

I’m quite certain this penmonkey will survive just fine.

Have you tried an alternate route into the industry? Please share your off-road antics in the comments below. As always, the more we writers share, the more we all learn.

6 thoughts on “Balls of Steel: Penmonkey Darwinism

  1. Nat

    Chuck does give pretty great advice. So do you, Jeanne 🙂
    Following you two was one of the first things I did after clumsily and unexpectedly stumbling into my first writing job a year ago. I’m currently in the ‘Oh-shit-what-do-I-do-now?’ phase of things, but your posts & tweets definitely help.
    Keep on keepin’ on!

  2. Jeanne Veillette BowermanJeanne Veillette Bowerman Post author

    Jan, being an extra is a great idea! Films are shot all over the country (and world), so it’s not necessary to even live in L.A. for that tip. Thanks!

    Cara, please keep us informed of how your career moves. I’m digging the angle you’ve chosen to launch it. Paying the bills while winning a few awards isn’t a bad angle.

    Vivi Anna, I’m getting loads of Canadians in my Twitter feed the past few months. You guys have a great support system for filmmaking. Anxious to watch you all break in.

  3. Cara Mumford

    Strange as it may sound, my alternate journey to becoming a screenwriter has been through art house filmmaking. I took my first filmmaking course at an indie film co-op with the intention of gaining some understanding of the whole process in order to become a better screenwriter. Five short films, several grants, countless film festivals and a few awards later, my art house shorts have been paying for my screenwriting. Partly thanks to the Canadian arts funding system that often covers my basic subsistence while I work on these films (and hey, once my bills are paid, I’ll find time to write one way or another), and partly thanks to the paid directing and editing gigs that have come my way because of those art house films (we’re not talking big projects or big bucks, but again, the bills get paid). I may not have won any screenwriting competitions or sold any screenplays yet, but I did get funding to write the first draft of my very first feature, so I figure I must be doing something right. The latest draft of that screenplay has recently been entered into its first four competitions and I wait to see what the future holds (as I continue to revise and submit that screenplay, develop my next screenplay, edit the latest music video I directed, and so on and so forth). It will be interesting to look back in five years and see whether I think my off road antics have led me to screenwriting success. Time will tell.

  4. Jan Militello

    New favorite quote: “It’s important to know you can survive as a screenwriter by doing it your own way.”

    Off road antics:

    One thing I occasionally do, which may be somewhat outside the norm for a screenwriter, is to be an extra on big budget studio films. While there, first and foremost, to be the best darn background possible; the knowledge gained in glimpses of what I consider genius at work – with the likes of Nolan, Soderbergh, Reitman and others at the helm – informs my writing.

    This informed writing, in turn, leads to opportunities to have my scripts produced. Additionally, the time spent onset as an extra increases my comfort level on those shoots.