So You Wanna Be A Game Designer
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Q: How did you become a designer? Can you tell us about the career path you took?
A: At age 9, I was playing an exciting game of boomerang baseball (catch-return-catch) with one of the kids in the neighborhood when he told me about some bizarre game of pretend with rules, called D&D. This was shortly followed by seeing another friend playing Bard's Tale 2 on his Commodore 64, which solved the problem of wanting to play D&D without having anyone to play with. So I designed dungeon after dungeon [and] sent a lot of crappy submissions to Dragon magazine, Palladium, and GURPS that were sent back with dismissive form letters. Eventually, I wore down the patience of some Hero Games guys and wrote some pen-and-paper Champions supplements for them. The pay was pretty lousy (when it happened at all) and didn't do much for a feeling of security in the grand scheme of things, so I asked the editors if they heard of any "real" jobs in gaming, to let me know.
One of the editors was in touch with Mark O'Green, who was head of Interplay's Dragonplay division, so I went out to interview with him. Mark asked me some hard questions (the answers for which ended up becoming the basis for Torment), but in the end, he figured I was worth a junior designer salary. So I took the job at Interplay and drove cross-country to begin my computer game designer career at Interplay Productions. From there, I worked on most of the Black Isle titles until leaving to help form Obsidian Entertainment.
So the short of it was, I was doing freelance game design for a while, did some pen-and-paper supplements, then used that to get a job in computer game design. It wasn't a bad way to go, but it's not the easiest.