D&D General From the Freelancing Frontline – From Hobby to Career

Originally, all I wanted from my game writing was to sell enough RPG game articles to afford a subscription to Dragon Magazine. But once I had done that, I found I wanted to write more. Much more. So, I kept sending pitches to Dave Gross, at Dragon, and began looking for other venues. I had long wanted to be a writer, but I had always expected to be a fiction writer... despite doing nothing to get my writing published. Now that I had proven I could sell written words, it seemed smart to update my plan to be a writer for game content and fiction, and send out every proposal I could think of for both. And knowing where to send those things took research.

This is the second article in a column by from Owen K.C. Stephens. Click here for the first column in this series.

I hadn’t done a lot of research in school. I avoided it, because I found it boring and didn’t like people telling me what to do. (I barely graduated from high school.) But I HAD learned the basics of how it was done, and had applied those skills to topics I cared about—WWI and medieval weaponry and armor, mythology, futurism, fortifications, and so on. Now that it looked like research could get me practical things I cared about, like knowing where to send words in exchange for money and geek cred, I was voracious in my appetite to do it.

I read through years worth of Writer’s Digests at the library. I made lists of contacts and submission rules. I read publisher information on every game product I owned, and many at the local game store. I sent out a TON of SASEs. I pitched everything I could think of, from more fantasy race name generators to short stories about sidhe brigades at the Battle of the Somme.

Every fictional pitch I sent out was rejected. Every game pitch lead to something I could make money on. That meant more and more, I was focusing on writing game material, because I kept having assured income available from that. In fact within a few years, I stopped ever trying to pitch fiction, or even write it. I shouldn’t have. It’s a mistake I still plan to rectify, but now I’m 20 years behind where I could have been on that journey. That’s not to say I’m not really proud of the game material I’ve created in those decades—I am. But I also like to look back from time to time to review what I think I did wrong (or could have done better), in an effort to develop my own best practices.

So after selling my first article to Dragon Magazine, I began to sell game articles fairly regularly. I was keeping my pace of 1,000-words a month (which seemed breakneck at the time). There was, of course, a long gap between when the articles were sold, and when they appeared. So while many of my family and friends were pleased by my literary success, it was all still very theoretical. But I knew I wanted this to be more than a side gig for me. I didn’t just want my hobby to be budget-neutral. I wanted this to be my career.

And I couldn’t do that on magazine articles alone. (I also couldn’t do that at 1,000 words a month, but I honestly had no idea how slow that was yet). I wanted to be on a career path, but I began to be frustrated with having no idea what the signposts were along a path for building an RPG career was. It was clear to me that to make a living at 7-cents a word (more or less, at the time), I had to have more regular work than magazine articles. I needed a company to give me a chance to write adventures, rulebooks, splatbooks – the “real” RPG products. Eventually, I assumed I wanted to be on staff at a game company.

But I had no idea how to make that happen. No one had game design classes at that point. I owned Nick Schuessler & Steve Jackson’s “Game Design (Volume 1: Theory & Practice)”, but there wasn’t much else out there that seemed to speak to RPG design. The professionals were better than I was, and I didn’t know how to gain the skills they had. There was some breakthrough I was missing.

I began sitting in writing seminars at every convention I could get to, and that WAS a good idea. They weren’t workshops at the time, at least within driving distance of central Oklahoma, so you could only learn what panelists thought to tell you, or that you could get in 1 or 2 questions about at a Q&A session at the end of a 50 minute panel. But it was a lot better than nothing. Mostly I didn’t even ask questions. These were, after all, professionals talking. I just had a few as-yet unpublished articles sold. I was a hobbyist, at best. I assumed the people asking questions were at least one rung up the professionalism ladder from me, and only dared raise a topic if no one else took the opportunity.


But I knew I was still missing some crucial link in the chain from hobby to career.

In addition to going to seminars, I had a lot of fun hanging out with friends at local conventions. One such friend was Carl, who I have known for well more than 3/4 of my life. I told Carl nearly everything, including my frustration not knowing how to move forward. And so, whether because he knew I needed to but wouldn’t, or because he just wanted the experience for himself, at one local convention Carl took the next step I hadn’t even thought of.

We were wandering around the hotel lobby around noon when he spotted the great Aaron Allston. Carl told me to follow his lead, and went up to the titan of gaming.

“Mr. Allston, we’re both big fans of yours. Could we take you to lunch?”

I was shocked at Carl’s chutzpah... but Mr. Allston was delighted by the offer. We did take him to lunch (when trying to decide where to go, our guest confessed he’d be happy just going to the Wendy’s we could see from the hotel parking lot... so that’s where we took him), and we had a grand time. We did talk about gaming and game writing, but we also just hung out with an awesome human being. And I realized what I had been missing. If I wanted to become a professional, I needed to meet and get to know some existing professionals, and talk to them 1-on-1, or at least in a small group setting. My own introversion, depression, and social anxiety be damned, this was clearly what I had been missing.

I owe Carl a lot, for having the nerve and brains to arrange for that meal. I repaid him four years later by totally forgetting to have him credited for writing part of the Everquest TTRPG book “Realms of Norrath: Freeport,” when he wrote big chunks of it because I couldn’t get it all done on my own.


Sometimes I am amazed Carl still talks to me.

Hanging out with Aaron Allston was a huge turning point for me. It showed me what I needed to do to make the next leap in my career. And a few weeks later, my subscription to Dragon Magazine advertised a great opportunity – the 1997 TSR RPG Writer’s Workshop, in Seattle.

Which there was no way I could afford to go to, and which seemed like the perfect next step for me career.
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Owen K.C. Stephens

Owen K.C. Stephens

Great article and enjoy the lunch thing. Reminds me of when Harlan Ellison walked up at a restaurant near the DragonCon hotels and sat down while he was waiting on his group to arrive. Asked what we were having and sampled it. Signed our badges and left us with a nice life long memory.
The name Aaron Allston rung a memory bell but couldn’t place it immediately....quick search and one of my favorite books from the late 80s, Grand Duchy of Karameikos, came up that he did. Still have it and will look through it when I get back to the house.

Von Ether

Great article! I wouldn't beat yourself up over the fiction, though. Most "new" writers don't break out until their 40s or 50s unless they have a luck, or a leg up -- and that's not impling those fortunate people lack talent or drive.

It's just that fiction is that much of a gamble, and the market is getting worse.

From the outside, the public focuses on blockbuster success stories that are outliers. Perfect example, Brandon Sanderson vs Matt Forbeck.

And don't get me started on reader's buying habits, like the people who will love a media tie in novel, but won't look at any other books by the same author.

Who knows, this might be your time to start. Give it a try and good luck!

Paragon Lost

Terminally Lost
Good read. :) Love the insight into a creators journey into making this hobby a career. Also, very cool about Aaron Allston, I'm a fan, so kudos to Carl for getting you to go up wto Aaron and do a lunch. :)

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