Planning
To plan or not to plan, that's not really quite the question. It's an individual thing and what works for some storytellers but will be a disaster for others. Some are great at playing it by ear, writing the story as they go. Maybe they have an over-arching plot in mind, maybe they don't. Some are at their best when they prepare detailed notes and plans and backup plans.
It's up to you to figure out how you work best, but don't start a game you can't finish. Whether you need time to plan or the energy to wing it, do it and dedicate yourself to the doing. An uncommitted or sloppily made game isn't fun for anyone. Storytelling preparation falls into one of three categories: seat of the pants, planning a level at a time, and planning way ahead for the whole game.
If you can make a game as you go and being able to come up with a direction and how to react to what the the player might do a any point in the story, then you rock. That's not easy; but if you're good at it, it could be an awesome game. Developing a game that way can be quite flexible and nimble. You can go wherever think the player can take you or go wherever a sudden thought takes you.
Those who take it a level at a time are pretty close, but when you start that level's game, you may have a plan; but, you may not know what the next level will actually hold, because you're waiting to see how this level goes. It's a little more structure than totally improvising, but you can still go in any direction because you haven't planned the next week or the week after yet. So, it could be a good thing; but, you have to watch about the possibility of revisine perhaps the previous week.
Here's what can bite you in the behind, though: You have a plot, say preventing [insert catastrophic evil here] from destroying [insert something nice here]. If you follow a tangential (slightly or indirectly related to the . . .) story – whether it was generated by the what you think the player might do or a sudden idea you may have – might move the game away from your plot too far. Then you have to figure out how to get back in that direction. You have to split your focus between advancing your story and reacting to whatever might happen in the game.
The real danger and the one that damages a game more – because those tangents and the road back to the plot can be a lot of fun – is that you risk going too are in thinking what the player may think and do while they are playing the game. Let's say you are reading a bedtime story to a child. The child keeps asking questions about what Goldilocks was doing in the woods and what flavor the porridge was and where the bears had gone all day and why they left their porridge on the table … You can answer all those questions and you can make as much of a story out of them as you like, but if you do, then you're not telling the child the story of Goldilocks and the Three Bears anymore. You perhaps have gone way too far from the plot and you might lose sight of it and then confuse the player with what the journey (mission) really is.
One storyteller told me that he felt he could never predict what the player would do or how the player would meet challenges in his game, so he didn't even try to plan most levels ahead of time. He just followed his plot or story. Because there was no planning or thought behind building the game, he just used the same bad guys over and over. The fights were pretty much the same with no surprises and not even much variety. My thought is that probably will not be a very fun game to play.
The player can easily be frustrated because they would have no idea where to go. He/she had to guess at what would lead them towards the plot. The levels of the game that had been planned more strongly were the best of the campaign, but others suffered. If you have decided to be a Storyteller, then tell the story. The players collaborate and weave their characters into it, not the other way around. Make things happen to the players. They don't know the plot and they can't guide the story. NPCs should come to them for help, villains should menace them, danger should court them. Bad stuff needs to go down and the player's part is to react to it. You take what you think their reactions might be and make it a part of the game, but you need to be active, not passive.
If you spend a lot of time planning, you have other issues to deal with. I know of someone who works best when he has the time to develop his story into a detailed outline. It's not unusual for him to spend more than a hundred hours on a game before he even begins working on the computer.
He usually ends up with NPC lists, maps, a high-level outline, a low-level outline, chapter by chapter notes, a second draft of those with the rolls and rules and stats and sensory details. The obvious downfall is the huge investment of time even before he puts the first segment or entity down in the map. A hundred hours? If you've got school, a job, kids, or even one of those social lives I've heard about, then you may only be able to spend a few hours a week creating a game. At that rate, it can take a year to plan in such detail. So plan ahead. What other problems can detailed planning cause? Well, if you get too attached to your plan or too rigid in adhering to it, then you could lose flexibility. Just because winging it may lure you into being passive doesn't mean it will, and just because you plan your game in detail doesn't mean you'll automatically become a dictator. Either planning ahead or playing it by ear can be great ways to develop a game and have fun, just be aware of the traps inherent to both and make sure you don't fall into them.
When in doubt -- C4 :heh, heh, heh:
-Jamie Hyneman