No regrets?

There's an interesting thread making the rounds on the gaming blogs (I picked it up at Treasure Tables, who is responding to Abulia Savant), asking people to list their regrets as a Gamemaster. Well, let's see if I can take a crack at this:

The top five:

5. "Akl and the Cuisinarts" (2nd Ed. D&D, 1980's). One of my first extended fantasy campaigns, and the first involving one of my best friends. Although he was a first-rate roleplayer, he had a terrible time dealing with the fact that D&D quite often came down to the d20, and in my zeal to keep him enamored with the game I'm afraid I fudged a few too many die rolls on his behalf, creating a tension with the other players that lasted for quite some time afterwards. It also seriously undermined my credibility as a GM who hesitated to let the dice fall where they may when the chips were down.

Part of this problem is my own basic inability to say no, a trait that I'm afraid has colored my skills as a Gamemaster over the years. Strangely enough, it was only when I started to teach Ancient Greek that I began to learn how to engage the people in the room without compromising the integrity of my source material, for when teaching a language at its most elementary level the students are either right or wrong. The trick is finding a way to keep your students motivated and willing to come back week after week in spite of the fact that their understanding of Greek isn't ever going to meet their expectations and/or desire. For a long time I had always thought that being a GM made me a better teacher; now I see that the converse was also in fact true.

4. Dekkar Kelrig Joins the Cirus (PBEM, 2nd Ed. D&D, Summer 1997). When my best friend from college and I found ourselves on opposite ends of the continent, we resolved to continue a solo D&D game we had started in a Clockpunk campaign world of my own imagining. The result was a narrative-rich storyline in which my friend's PC, a bounty hunter named Dekkar Kelrig, stumbled upon a novel solution to a seemingly impossible plot gangster plot: he shot his antagonist in cold blood and ran off to join the circus in a foreign land.

The PBEM format lent itself very well to this storytelling change of pace, as instead of dodging crossbow bolts and getting pummeled by thugs our antihero now found himself in a setting that could have been lifted out of a Robertson Davies novel, and over that summer we fleshed out the architecture of Dekkar Kelrig's long-term attempt to exorcise his old demons and crawl out of the personal hell he created for himself. Whereupon, of course, we abruptly stopped playing the game. Had it grown too plot-heavy? To be sure, each update on either end was more like the chapter of a fantasy novel than an actual game. But I suspect that events in my own life (which were getting a little weird at the time) had prevented me from continuing the story just when it was getting good - that and my then-inability to bring anything I started to a meaningful conclusion.

All of that being said, I got a lot out of this abortive campaign, as did my friend. For my part dedicating myself to regular updates for an PBEM of this intensity helped me developed the narrative and world-building toolkit I would need to make my first attempt at writing a fantasy novel, which I completed last March after three years and one that I wrote a sequel to during NaNoWriMo 2006.

3. Taking it personally (2nd Ed. D&D, Summer 1988). In the last extended fantasy campaign that I ran for my old hometown crew there was a kid who wore the term Munchkin as a badge of honor. A powergamer to the core with no discernable roleplaying abilities whatsoever, the constant irritant of his presence was mitigated by the fact that not only had his own car but an apartment as well - two much sought-after commodities that allowed him to pull the same manipulative bullshit in the real world that he did in-game.

This friend of mine was playing a wizard that summer, and since he was using the Academician kit from the old Wizards Handbook he got it into his head that he was going to research how to make... wait for it... gunpowder. What, you're not surprised? After throwing up every imaginable roadblock I could think of to keeping him from doing so - from the esoteric nature of the knowledge to the relatively scarceness of sulfur in my world, a kludge which persists to this day as a feature of that campaign setting - eventually I caved and started to let him amass a whole arsenal of black powder in the hold of the sailing ship the party had taken possession of a few adventures back.

Angry that he'd worn down my resistance and annoyed at him in general for various matters both in and out of game, I decided at long last to take my revenge on him. Remembering that the party had a necromancer foe who actively scryed on them (and what's more had a magical mirror that allowed him to cast spells into the area he was viewing at the time), I ruled that at some point he must have noticed that his magical opponent was brewing up enough gunpowder to blow up his entire tower. So without so much as a warning, I had the evil wizard cast a fireball through his mirror and BOOM! the whole ship goes up, killing pretty much everyone on board - including my friend's NPC girlfriend and a new party member who had just set foot on the boat.

Oops. Well, someone managed to get away from the flaming wreckage and retrieve the rest of the party's charred corpses, and since this was old school D&D no one really blinked twice about the thought of having their characters raised or resurrected in order to continue with the game. At this point everyone but my wizard friend was aware of the fact that I had been out to get him specifically, and amazingly they were so eager to see his character get the boot that they were willing to lose a point of Constitution and hazard a Resurrection Survival roll in order to do so. There was barely-restrained jubilation when he was the only person to blow the roll, and although this act on my part is a celebrated piece of gaming lore among my circle of friends, it didn't feel quite right then and it still doesn't sit well with me now.

2. Failing to pull the trigger (Homebrew Fantasy System and Campaign World, 1996-1998). This is more of a designer thing than a Gamemaster thing, but insofar as this system was concerned the two were intertwined. My college friend and I had been evolving a FRP system out of 2nd Edition D&D for years, and over a three-year period we attempted to get this thing from the drawing table to the gaming conventions in what turned out to be epic fits and starts. The 1.0 version of the rules - which were based on a 2d6 mechanic, similar to Traveller - were something we had managed to get to the playtesting phase before we chickened out and fled for the relatively safe comfort zone of academia (me) or blew out of town entirely (my friend).

After realizing that this was too good a system merely to abandon like this, and having found inspiration for my part from my then-fiancee - who although not a gamer found the work I had done up to this point absolutely fascinating and encouraged me to get it into print - we resolved to try again in early 1998, thus crafting the 2.0 sourcebook. Neither a student any longer nor gainfully employed yet that winter, I worked like a madman, copyediting the mechanics my friend wrote up and sending pages after pages of campaign world background for him to do the same. It was again when we hit the playtesting phase of the development that everything seemed to fall apart again. With the end in sight, it was as if we suddenly were actively conspiring against ourselves to prevent us from having a salable product for the next con season, and then the moment was lost.

Believe it or not, we almost attempted a 3.0 edition, but then 3rd Edition D&D hit, and unwilling either to market a non-d20 fantasy product or retool what we had to accommodate the OGL, we let the project go out with a whimper and not a bang. My friend did manage to start up a campaign using our 2.0 rulebook a year or two back, and after some tinkering with the mechanics it runs quite well, but the idea of giving it yet one more go (especially now that d20 is at its nadir) is something that holds no appeal to either of us. When we attempt to do a post-mortem of the venture, my friend is always quick to fault the system, but now that I've had about ten years to think about it I think the real failure was one of execution. If only we had figured out to silence the internal critics telling us that our product was crap and just starting selling it, who knows what might have happened?

1. The death of my friend Art (Summer 2004). My ultimate failing as a Gamemaster, however, came in the form of a real-world tragedy: not being in attendance at my friend and long-time player's funeral when he died unexpectedly at the end of the Summer of 2004. Art was the consummate gamer, willing to give any system a try and unwilling to apologize for his love for roleplaying when so many of us treated our passion for gaming as a dirty habit best not shared with the general public. Art was a writer, a poet, an amateur filmmaker and probably would have been one hell of a game designer, had he lived long enough to see just one of the myriad ideas he'd fleshed out over the years go to print. He was a hell of a player, and a right proper GM in his own right, and we still miss his presence when we gather around the table to game. While at the time there were serious extenuating circumstances that kept me from being there with the rest of my hometown friends and fellow gamers, to this day I would give anything to somehow change that decision not to go.