I started role-playing at the age of five without firm rules, any way to determine the success or failure of our stated actions, and little framework for a story. We called it Cowboys and Indians, and while it wasn't the most rewarding role-playing experience I've ever had, it did have a significant impact on me.
At the age of fourteen I discovered console-based RPGs. I loved the hell out of Dragon Warrior and Final Fantasy I, and played them for hundreds of hours teasing out every last spell, treasure, and secret. But, eventually my friends and I ran out of console RPGs (little did we know that computer RPGs were at the height of their popularity).
My best friend and I decided to draft a story for a blockbuster console RPG. We set to work at it at once, and spent months brainstorming story events, creating monsters, magical items, plot hooks, and fully fleshed-out three-dimensional playable characters and NPCs.
All of that out of the way we realized that we didn't have the other skills needed to make a console RPG (art, programming, or money). We languished for months trying to figure out how to make use of literally hundreds of pages of dialogue, monsters, and character stats before finally realizing that we could play out the scripted dialogue and combats without the use of a computer.
I programmed a TI-84 with attack and defense macros and we dusted off an old chess board to use as a battlefield. We enlisted the help of a third friend and started reading lines of dialogue and diving into the slow, mechanical combat of a table-top console RPG.
Soon we became aware of what was missing, spells lacked important attributes like range or area of effect (which were unnecessary in a console game) and we had to scramble to revise them. We noticed that our characters were stationary on one side of the board "attacking" monsters on the other side of the board so we added movement rules and restrictions. Later, we added collateral damage rules when we realized we were repeatedly blasting certain areas with fireballs. Our table-top console RPG was turning into something very different from what we envisioned.
We finished the main story and made new peripheral characters, but soon the game went stale.
In the summer of the year I turned sixteen I was walking through Toys-R-Us when I found a D&D board game. I carried it around the store reading the box, back and front, over and over for more than an hour before I decided to buy it. I took it home and hunkered down over the manuals for a few days.
I had a hard time with combat rules like THAC0, got confused about saving throws (I thought you needed to roll low to pass them), and nothing enraged me more than the idea of hitting a monster then rolling a one for damage. Regardless, I asked my closest friends to play. We agreed that it would probably suck, but gave it a shot anyway.
After the first combat we realized how similar it was to what we were doing a few months earlier.
I ran them through the first dungeon giving them far too much treasure and so many magical items that the old +1s and +2 daggers were barely worth using as toothpicks. My players and I learned quickly from our mistakes, though it still took several years for me to go from being the kind of DM that runs a series of dungeons to the kind of Storyteller that runs a game world (no thanks to the D&D manual which stated unequivocally, "The world outside of dungeons is unimportant aside from the towns which the characters use to resupply for their next dungeon adventure.").
Later that year we met a group of AD&D Second Edition players. They seemed to be breaking every rule in the book, but it was so much more interesting that way. They introduced me to Shadowrun, a high fantasy, post apocalyptic, dark future game, which helped me break away from the D&D mindset (please hold the flames, I have come to respect D&D for what it is).
After running Shadowrun myself I became ravenous. I looked in every darkened corner of any gaming shop within driving distance for the oldest and most obscure games imaginable. I read (and sometimes ran) Star Wars d6, Star Trek, Battlelords of the 23rd Century, GURPS, Rifts, Toon, Call of Cthulhu, Paranoia, and a hundred others.
After I graduated from high school I was introduced to Vampire: The Masquerade. This was another massive sea change for my running style. My players had far more cinematic control over the game, and even carried some of the responsibility for creating the story themselves (especially once we got ahold of Mage).
During these twenty years of game design, playing hundreds of sessions, and running thousands I've learned out a trick or two that have made my games more enjoyable for me and my players. I plan on sharing many of them here, and I hope you'll share some of yours with me as well.