Paraphrased/condensed from a similar thread:

Weight goal - 225 by Thanksgiving. It's a lot to lose, probably around 70 pounds or so, but I can do it. It's 1.47 pounds per week, definitely doable

Fitness
Right now
- workout three days a week, a mix of strength training and cardio. May increase this to four days a week.
- Track food intake religiously, end day under caloric allowance.

Future
Commute three days a week when Spring arrives (starting as soon as possible, weather dependent).
Get in good enough shape to do the Dairy Roubaix (4/16)
If personal schedule allows, do the Bear 100 (5/24)
Join a local Bike Club, ride often with the club.
Do either the Udder Century or the Ride for the Arts on 6/1
BayView Bike Classic on 7/13
Cream City Century in August
MS Ride with my son - August
Race as many CX races in the fall as possible.
Ride 3,000 miles total.