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? Let me give you a couple examples. An acquaintance of mine has three children, and in my view, is financially prudent in all matters except for one. And this single weakness has caused her to continually have trouble with high levels of credit card debt. She’s had this debt problem as long as I’ve known him and his only weakness is a particular self-help seminar. At least once a year, if there is room on her credit card, she attends one of these seminars and charges it all to a credit card. I don’t see her do anything with the information that she learns, and she feels it is so important, but I fear that she is sacrificing her family’s financial future. I’d rather not see any more exposés about non-profit organizations spending their donations on supercomputers to analyze direct-mail campaigns instead of their stated cause. In another example, an acquaintance’s grandmother has a weakness for requests that she receives from left-wing political organizations. If a direct-mail piece lands in her mailbox, then they are guaranteed to receive some donation from her – no matter that she can’t afford it. And like a good poker player sensing weakness, the fund raisers now flood her mailbox with donation requests. Leaky Wallet Syndrome doesn’t only afflict individuals. A family-friend is a business turnaround consultant for private companies. He says that the majority of the time his services are called during the third-generation from the business founder. The founder builds a successful business and the second-generation coasts on this success, and is mentored by the founder. But by the third generation, the business is supporting so many family members on the payroll that don’t contribute value and family infighting prevents any efficiency or reform, that only Herculean effort from an outsider can save the business from so many forms of overspending. You don’t have to look far from home to find Leaky Wallet Syndrome (has anyone seen my Ferrari? I mean my Ferrari keychain with a used Honda key?), but all the leaks in your psychology need to be plugged before you can successfully move toward your financial goals. And this effort also helps prepare you for any windfalls that would quickly leak from your wallet.