If your character was a plumber, he wouldn't have to roll to see if he could figure out what was clogging the sink drain. He deals with that sort of thing every day. But if it came to something unusual, say a student had dropped a lit cherry bomb down a toilet in the school bathroom, well a plumber might still have to roll, but he would have a much easier time figuring out the problem than a teacher. In the old days, the DM would just assign these rolls accordingly without referring to a stat sheet.
To help explain this further, he ran a little roleplaying session with me. I was a thief, number19. Old number 19 wasn't around anymore, so I had just been promoted. I was supposed to steal a necklace from a wealthy patron in the city. Here I was looking at the manor house and walled courtyard from a hilltop. I didn't see anyone around, and I'd heard the old lady was out shopping in the agora, so I decided to break in.
I made a horrible mess of the job. The lady wasn't out shopping; she was in her courtyard, and tried to attack me with pruning shears. I didn't plan on the bodyguards. I tried to tell them that the lady was in the market and needed help, but it didn't fly. I ran for it. There were two doors to the house. I chose the left. I found her room, and grabbed some jewelery only to realize that the windows were just were too small for me to escape through. I was blocked in by the body guards. One good punch and I ate it.
Here's the thing that amazed me. This was extremely fast paced and heart racing, and Carl made up everything on the spot. We didn't have dice with us, so whenever I got in a situation where I had to fight someone, he played rock-paper-scissors with me. I had three hit points. If I lost three times, I was dead. The lady had one hit point, while her body guards had three as well. I think I got lucky and managed to take out one of them, but two were too much for me.
This was magic. I feel like I finally got to experience the tao of a good game master. The rules are just guidelines, and ultimately don't matter. The heart of the game is much more akin to a sparring match than a board game. It's like the fast paced narrative of a debate--a battle of wits, or thinking on your feet with only confidence and creativity at your disposal.
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