Q&A with a Seasoned Veteran of the WEbook Writing Contests: SigmundSquirrel


20100216writingchallengeblogIf you’ve been knocking the digital pen to paper at WEbook for a while, there’s a good chance you’ve seen the name SigmundSquirrel before. He’s been a WEbook member for over two years, and in that time he’s been an active participant in the community, PageToFame, and the series of WEbook writing contests.

Not only as he entered a bunch of the writing contests, he’s won his fair share of them as well. We decided to check in with ole’ Sigmund, get a sense of the man behind the victories, and see what else he’s taken away from the contests (besides a bunch of P2F coupons).

Tell us a bit about yourself. What do you do besides write?

I'm the design director and a developer for an interactive digital agency, making games and branded entertainment for web and mobile. 

How did you first hear about WEbook? When did you join?

When I first began looking at online writing communities, I Googled and found WEbook. I immediately liked the clean, minimal design and the PageToFame concept, so I joined back in March 2010. It looked like a place where I wouldn't mind spending a lot of time.

What was the first WEbook writing contest you entered? How did you approach it?

The very first writing challenge after I joined was The 150-Word Short Summary Challenge. The timing was perfect. I'd just begun thinking about an idea for a novel and had entered the first page in PageToFame. I wrote a summary of the idea, The Inner Eye, and entered. It became my first writing challenge win.

How have the writing challenges affected your longer works?

The idea for the Summary Challenge turned out to be bigger and more complicated than I thought, and I'm still struggling with it. When I get lost (which is frequently) I return to this summary to remember the tone I'm looking for.

I continue to use the writing challenges as a way to work on specific problems with my work-in-progress. I wrote an ending of The Inner Eye for the 100-Word Ending Challenge which I like but may not use.

For the OK Cupid Challenge, which I won a few months, I returned to the setting of The Inner Eye, with an entry called Always Something Doing.

I used a lot of the research I'm doing for Boston, 1947. My novel takes place in the summer, but I found out there was a record-breaking snowstorm on Christmas of that year. I couldn't use it for the book, but I immediately thought of it as a backdrop when your challenge set up the parameters of a winter romance. The character of Dolores is from the novel, as is the neighborhood and theater.

What’s your favorite submission to a WEbook writing contest?

One of my favorite (and I think, best) writing challenge submissions was for The Character Creation Challenge. I chose a minor, colorful character from The Inner Eye. You had asked for a bullet list of 12 attributes. Instead, I wrote a short story that highlighted all the attributes:

This exercise really opened up the character for me. I gained such a greater understanding of him that I have a second novel, a sequel to The Inner Eye, in the note stage with Eliot Stark as the main character, exploring the plot from this short character study.

What do you think has changed the most about your writing after participating in the WEbook writing contests?

The writing challenges have imposed discipline on my sometimes florid prose. When I see a new challenge, I write down notes and sentences in a text-editing program to see what pops out of my head.

Once I focus on an idea and begin putting things together into a story, I usually find out I'm several hundred words over the limit. After I struggle to cut down to 300 or whatever the limit is (and I'm usually still over) I find out the writing becomes stronger and more forceful. I'm trying to impose a similar discipline to my longer writing. An example is the original Inner Eye, which made it to Rounds 1, 2 and 3 in the PageToFame contest. But I've now gone full circle with a new first page in a more minimal voice that I just re-entered in the contest.

Have you broken any new genre-ground during the contests?

The other writing challenge I developed into a novel idea was The Wyrm In Rat's Alley, from The Dragon Slaying Challenge.

This was my first attempt at sci-fi/fantasy, which I combined with a noir voice. I dropped the plot idea but kept the character for a PageToFame submission called Blodryne, which made it through the first round. I'd been struggling with the first chapter for Round 2, and when I recently wrote another writing challenge entry for The Backstory Challenge, called The Big Pharma, I reworked the characters and setting and came up with a new opening that solved my problem and opened the story out for me:

It was a winning entry. It's interesting that both stories are a year apart and you can see the slimmed down writing. The Big Pharma maintains the tone but has a more forceful forward momentum. I attribute this change in my writing to WEbook and the writing challenges.

Thanks for the great answers, Sigmund. Very cool to hear your experiences broken down into such detail.

Stay tuned for more WEbook writing contests and other scribe-related opportunities.

And if you’ve taken home a handful of PageToFame coupons yourself off these contests, you might be hearing from us in the future.



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  1. OMG Sig you're famous!!
    Enjoyed reading this and seeing how you've progressed through the contest entries. I have also found them remarkably helpful and it's great to see how other people tackle the paring-down process as well.
    Cool stuff, bro. Rock out with your...oh wait, I have to be polite here. Um, rock on.


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