I have the spending issues as well, and the mountain of debt to show for it. I just bought a car and rolled all the upside down debt on the old one into the new loan. And oh yeah, that's my 6th car purchase in the last 5 years. That upside down debt just floats from loan to loan, and keeps growing. I bought gap insurance this time. That means if the car is totaled in a crash, they will pay out the balance of the loan, even though the amount from the insurance company wouldn't be enough to cover it. I don't want to put a curse on myself, but maybe that would be for the best?

It was strange though, this time. When I bought the car, I didn't really care. I wasn't elated about it. My wife was excited about it, even though she's definitely felt the distress from my reckless purchases. I like it, but it's just kind of no big deal. With all the other purchases, I was over-the-top elated and obsessed. I guess when your spouse is really into it, it takes all the thrill out.