Financial stewardship of a business empire or $100 bill require a particular psychology if they are going to survive over time in the same hands. The lack of this same psychology is why most lottery winners cannot hold onto the giant sums of money they receive; and I call this psychological mind-set the "Leaky Wallet Syndrome".
The difficulty with holding onto money is that it only takes a single weakness to lose it entirely. By weakness I mean that something has caught your eye that is so desirable that you will buy it spite of the fact that you cannot afford it. Whatever this purchase or payment may be, it psychologically reaches your personal threshold where having something right now is more important than having something tomorrow. There is a trigger that sets aside your normal, balanced decision-making with instant gratification. In my opinion, it is similar to dieting in that you have to eat food, but there are consequences if you continually eat even a little too much. Likewise you need to spend money, but there is a predictable consequence if you continually spend even just a little too much.
Let me list some of the common categories where people could have financial weakness: vacations, clothing, cars, shoes, personal electronics, charities, collections of any kind, books, Christmas gifts, watches, pets, jewelry, relatives, dining out, boats, hobbies and sports activities. And these are only single leaks in your wallet, if you have many of them your wallet could be in more serious trouble.
If you've never felt like you've had much "extra" money, you may not be aware of what your financial weaknesses may be. They may not show up until you receive a sudden windfall (annual bonus, tax refund, pay raise, inheritance, lottery winners), and you are not familiar with or prepared for your psychological pressure to spend money. If you want to know a few of your weaknesses, think about some of the items at the top of your list that you would buy if you had the money. How many of these items would seem like reasonable purchases to friends and family vs. how many would seem like ridiculous extravagances?
If you are still not sure if you suffer from Leaky Wallet Syndrome, your checking account may tell you: Do you have money leftover at the end of every month? Are you unable to payoff your entire credit card balance each month? Do you have any past due bills? Do you hide your checking account or avoid balancing it?