Are you me?
To answer the original question; I think it's easy to book the first show if you know where you want the story to end up. I'll usually go through this process:
1. What big match would I like to present in four/five shows time?
2. What would make this match really interesting?
3. What angles would make sense (taking into account the gimmicks, wrestling styles etc)?
4. Who else could get involved in the angles?
Once I have that outline everything else falls into place. Then I start thinking about the gamey side of things; how to get momentum up, who needs to be in the storyline, how can I best use the guys/girls who are going to be involved.
Usually by doing things this way I also get loads of ideas about what could happen after. It ends up that I'm rarely at the end of the story not knowing where to go next, i'll have a few ideas of the consequences of the last story.