I couldn't wait to pay off our mortgage. Our financial guy told me I need to get another mortgage and put the money in the market (which he managed, of course). I told him my peace of mind was way more important that making more money, at that point in my life.
I have some in-laws whose dad sold a company (many Ft. Wayne people would recognize the company, so I won't name it her) and split the money with he and his kids getting equal shares. If was a large amount each - large.
One of the kids kept his job, invested the money, and is now very wealthy, living on a lake in northern Indiana, but still generally living what we would consider a simple lifestyle, considering his wealth. On the board of several companies, but retired and living the good life. He was the one considered not-so-smart by the rest of the family.
One invested in real estate and lost his ass in 2008. Still working and living in his father-in-law's house.
The third on built a McMansion, quit her job, her husband quit his job, and they generally lived like they were millionaires (which they were, but with no income other than their investments). They eventually had to move out, get jobs, and now live in a 3 BR ranch.
The last 2 were considered the 'smart' ones. Go figure.
Like you, I could afford about anything I want, but can't bring my self to pull the trigger on things like a sports car that I'd really like to have. It also pains me to pay for a nice vacation, but I find that easier to do than buy luxuries items. We made many attempts at a budget, but neither one of us were detailed enough to record and stick to it. We mainly acted as watchdogs on each other's spending. lol