I started writing in third grade, so far as I can really recall (though maybe my parents or grandparents would tell another story). Our teacher had the whole class write "books" which were "published." Being obsessed with dinosaurs (seriously, I wanted to be an archaeologist/paleontologist in kindergarten and used those words, to much laughter from the other kids, to tell everyone so), I wrote a book called "The Futuristic Dinosaur" in which a dinosaur was teleported to the modern day, learned to speak English, and went to school with a teacher named after my teacher. I still have the cloth-bound book that I got as a result. Even though I'd walk away from writing for long periods, I kept coming back to it, and I doubt I would have had that in my life if it hadn't been for that book.
I was a rather awkward child. I was sure I was "normal" in terms of schooling until about 4th grade, but felt like the kids laughed at me so often that I must be "weird" socially. And that became a self-fulfilling prophecy. The more awkward I felt, the more awkward I became. And then I figured out, via testing, that I wasn't "normal" in terms of schooling. I was "gifted" and needed to be in "special classes." Which meant getting up and walking out of "regular class" at a specific time. Which is about the worst thing you could do to a kid who felt like an outcast already. I tried to overcompensate by being "the funny kid" but I was pretty awful at that.
In 5th and 6th grades, I was introduced to the Robotech RPG and then Battletech by my older cousin. I started reading the Battletech novels and entered two separate writing contests while writing fiction based on the Battletech unit (The Stanley's Callers) my cousin and I had come up with (we had t-shirts, deal with our awesome). Those entries went nowhere, and coupled with a major knee surgery, the divorce of my parents, my dog running away, and having to leave all my junior high friends while heading to high school, I pretty much stopped writing and barely roleplayed at all (though I kept collecting books, for which I am now quite thankful).
It was almost a the end of my Freshman year (though at the time it felt like decades) when I met the core group of friends which would grow into my Terminus roleplaying group. One of them roleplayed online, as well, with people from both the US and Canada, and after working up the courage, I joined the forums (hosted back in the day by ebulletin if I remember right). This dovetailed with my idea to write fiction based on Robert Jordan's Wheel of Time series. Kids, don't let people tell you fanfiction is bad; you should aspire to come up with your own stuff, but world building is hard and characterization is more important, fanfiction is like training wheels for writing. So is roleplaying, which does many of the same things as writing fanfiction; using a pre-created setting, sometimes pre-created characters, and putting the writer's/player's character into the center of the action especially when it can serve as wish-fulfillment. Definitely aim to take the training wheels off, because you won't get rich trying to sell Harry Potter fanfic, but use the resources you have to practice.
When I went to college, I continued on in the "be what I'm not" compulsion that I'd formed way back as a kid and tried to be a computer engineer. I was pretty bad at it; I passed my classes, but I often struggle to make my code work, got C's on tests, and fell asleep in class the only time it's ever happened to me. After all that angst, I was done. I switched to being a creative writing major, gave up dreams of getting rich off writing software, and got back to writing. I wrote a lot, too. I was writing at least a page a day roleplaying, plus writing out elaborate backstories for those characters, and writing papers for class. I also made more friends who roleplayed, which would form the core of Sunday Game Group later on.
I took five creative-writing specific classes in college. Two were fiction-based, two were poetry-based, and one was autobiographical. I mention this not to tout my creative writing genius or education (because seriously, five classes in which most of the class had no major interest?), but to relay a story. My advanced fiction writing class was the second time in my life (and first time for fiction) I've been accused of plagarism. Afte the professor praised a myth-style story I'd written as being "right out of the Pohpol Vu," a classmate asked me if I'd really written it and where I'd gotten it from. It was pretty much at that moment I decide, for sure, that I'd be a successful writer someday. I was fairly furious that he'd question my skills and honesty that way, but figured if people assumed I'd stolen published work, I must be producing publishable work.
The key drawback, I think, in my writing over this period was self-motivation. If I was getting feedback or writing collaboratively (in other words, the things I got instantaneously from roleplaying), I could write prodigiously. If I was feeling a strong emotion, I coukd crank out 500 words in minutes. But when things were just "fine" and feedback was sparse, my writing would crawl to a halt. It took an odd writing gig for my job to change that. I worked for a now-defunct tutoring company which focused mostly on college e trance exams. I got offered the chance to write material for our new ACT textbook, which was a chance I jumped at as I could claim it as published work (to my knowledge, it never got to that stage). I wrote six pieces and 120 or so questions for that project but got minimal feedback. What I did get, though, was practice writing to a deadline and getting paid for my writing.
That led to me applying for a blogging job at a page-click-for-revenue news site covering roleplaying games. I quickly discovered, though, that my pageviews weren't worth a consistant value and that they'd hired another local writer to cover the same material as me in the same local area as me. I quit within a week. I created this blog but let it fall into disuse as I struggled to write consistently. I kept roleplaying, though, and eventually things came back around.
I got in the habit of telling my girlfriend, who became my fiance and then my wife, stories upon request, which challenged my ability to come up with coherent and compact stories. I needed to come to a point swiftly but still make the story engaging. And then I attended Blizzcon 2011 (actually, I've been to every Blizzcon but the first). There, I got to see a talk with the folks who write novels for Blizzard and heard how a past winner of the Blizzard Writing Contest was now writing fiction for them. Later in the sane day, I got to chat a bit with Nate Kenyon when he signed my copy of StarCraft: Ghost: Spectre. Those two events gave me a kick in the rear. I was determined to win the next BWC. Unfortunately, the next BWC hasn't happened yet. But in the interim, I finished one StarCraft-based story and made great progress on a second. They've integrated the lessons I've learned along the way and I feel proud of both. If nothing else, I could submit one or both the next time a BWC occurs and feel I gave it my best efforts. Similarly, the exercise of writing frequently inspired me to ressurect this blog in an effort to make connections to folks with similar interests.
So that's a long ramble on how I got to where I am. I'm not really published, rich, or famous. But I'm happy with the path of my writing and hopeful for its future. And at worst, I can use those skills to entertain myself.
TL;DR: I like writing and roleplaying, am happy with both, and can talk at length about it.
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