Sounds like 20 years in the military is the goal then. They can actually get you to those goals. $100k a year by 40, as long as you are an officer, no problem. Being a rich dude who doesn't work, not to bad considering you can retire after 20 years, roughly around 42 depending on your age now, and come out with a 50% pay retirement package, which is around $60k a year, backed by the US government.

I know it sounds like a long road, and it is, but it is worthwhile. You will have something that you can be immeasurably proud of for the rest of your life. Plus if you pick up a good "hobby job" to work at after you get out, you only are adding to that $60k. Hey, I'm just saying.