When I began this long road, I was in elementary school. It was third and fourth grade that saw me enter the world of fantasy roleplaying, though I wasn't using Dungeons and Dragons. Instead, I wanted to play games with my friends like the roleplaying games I played on the SNES, and I made up a ridiculous set of rules to do. You see, I had seen an old Dungeons and Dragons manual at my grandfather's house. Asking around as to what it was, I was told that it was a game that you play with pencil and paper with your friends.
Forgotten Realms was the first D&D product I ever bought, followed rapidly by the 2e PHB and DMG. I was in fourth grade, and I was a tyrant of a DM, angrily blasting players into greasy smudges when they made fun of Elminster or irritated me with backtalk. I was a child-DM and they child-PCs, so perhaps it was excusable.
That was the start of some kind of mania that has remained with me for the rest of my life. Shortly thereafter I became convinced that I needed to learn more about the middle ages to my D&D experiences better. I was a voracious reader, and I devoured every fantasy in the library and read the Lord of the Rings once a year to keep it fresh in my mind.
I read Villehardouin and scrambled to find history books. I became, as it were, obsessed with the period. This obsession was founded on learning how to better describe the fantastic worlds I dreamed of in D&D, to know how people lived in the Middle Ages and thus to be able to formulate true and proper worlds that were based not only on whatever fantastic assumptions I cooked up but rather on real information.
When I went to film school, history still clung to me. I spent a lot of my free time reading history books; my D&D days had dwindled, and my group had long since split up, leaving me without an outlet. It wasn't until I graduated that I realized I really wanted to simply study the Middle Ages.
That is how I became a historian, though now that I am having great trouble getting into a Ph.D. program it seems that this dream is fast retreating from me. So here I sit, a DM with an MA, writing fantasy literature and using my knowledge of history to produce a better D&D setting. I have made the journey from hobbyist to historian and back again. A strange journey indeed.