I am also a very goal-oriented person, so I need to have a constant list of races and times in mind if I'm going to actually work toward getting better. I have the drive and talent to do well at this, I just need the motivation to work toward it.
So far I am signed up for two races - Aurora Turkey Trot on 11/26/09 in Aurora, Ohio - 4mi, goal time: 45 minutes, and the Mardi Gras Rock-n-Roll Half Marathon, 02/28/2010 in New Orleans, LA - 13.1mi, goal time: 2 hours, 30 minutes. I haven't actually registered for the Mardi Gras one but I will soon.
Come next summer, I'm planning to do the US Women's Triathlon Series sprint tri in Naperville in the middle of June. I'm already familiar with the course but the swim is longer (750m vs 400m, which I've already done). I'm excited for this one.
I will also probably do the Naperville sprint tri again, depending on when the Cleveland Tri is. I'd like to do that one.
Eventually, I will do the Chicago Tri, The Disney World Marathon (you run through all 5 parks!), the Chicago Marathon, and something in Denver. I'd love to see how I fare up in the altitude!