I have a close friend/ex-coworker that is like that with money. He was a EE that was earning around $80K/year (20 years ago), a great salary for the area, had already gone through bankruptcy and lost his house 5 years earlier due to poor financial decisions. He was able to buy a decent doublewide on +/-23 acres way out in the sticks about 3 years after bankruptcy with "special" financing. We used to do lunch often and I'd hear him piss and moan about his finances a couple times a week. I was getting ready to quit my career to make the great leap to do my dream RE project. He was envious, wished he could do something like that. I pointed out that he could, he had 23 acres he could develop and he wouldn't have to quit work to do it. "Oh no!, couldn't do that" he said, "I love the acreage and privacy". A couple of months later he came around to embrace the idea. So I helped coach him through the development process, he made at least $250K profit on that small project over a 4 year period. He built a new 4600sqft colonial for his family on one of the lots and sold the doublewide (for more than he originally paid for it with all the land). In the meantime his father-in-law sold my friend their family camp on a big lake for $60k and financed it for him. About 10 years later my friend was already behind on paying that camp loan, so he decided to sell it for IIRC $210K! He had decided he wanted to work for himself, get out of the EE rat race, sold his big colonial home for more than twice what he had into it and bought an old variety store, proceeded to become owner/operator. After about 8 years of that he wants out of it, he's poured every penny he had into it and continues to operate at a loss. He made many improvements and has had the store listed for well over a year with no offers near what he was asking. He has used most of the credit available to him and is desperate to turn a profit or sell. The guy has had so much money since his bankruptcy 25 years ago, yet it runs through his fingers like water. It kills me to watch him. He has always had shitty cars, a shitty house (except while he had that colonial), no time to enjoy the nice camp that he eventually sold, almost always no money to make good investments, always relying on revolving credit, a stressful life and now medical issues as a result of pushing himself and the years of stress. Flat broke, stressed out, a stuck owner operator that wants out in his 60s. He has told me more than once he would be way further ahead if he hadn't bought the store and had done nothing in all that time. Some people just never get it even when you show them the way over and over. We are still great friends and I truly wish him the best, it kills me to watch him fail. It is hard to believe such an intelligent person can be so stupid with their finances.