Learning to Say “No” After Winning the Lottery

“No” is the first word every lottery winner should learn to say. Unfortunately, even a multi-millionaire’s life is full of compromises, and nobody can please everybody all the time. But not surprisingly, lottery winners are regularly approached with favors and expected to provide financial solutions to problems that may not otherwise concern them. And although the desire to help those around you is a noble one, it is also one that can easily backfire if you are not careful. Giving money to anyone who asks for it might temporarily win you friends, but it could also permanently drain your bank account and leave you unable to even help yourself. Conversely, refusing to help anyone could potentially leave you rich but without many friends to share in your happiness. This conundrum can undoubtedly put recent lottery winners in an awkward position they are not used to experiencing.

Whether an immediate family member is in danger of losing his/her house or your third grade gym teacher’s dog needs an expensive operation, it can be very difficult to decide who deserves financial assistance, under which conditions, when to provide it, how much to give, and how to go about doing it. Frankly, the simplest financial policy would be to bluntly refuse all requests for money or gifts. But, of course that doesn’t always play out very well in the real world, so it is important for most people to strike a balance.

How can lottery winners escape the guilt and the sheer awkward nature of refusing some requests while accepting others? Luckily, there are strategies that can help people who have a hard time saying “no.” One such strategy is to simply avoid saying “yes” or “no” and, instead, to default to a “maybe later” position. Indeed, this may sound a bit childish at first, but aren’t adults essentially just children who have grown up to adopt more advanced methods of realizing an evolving set of priorities?

The “Maybe Later” Approach

This is a method that can be used not only to diffuse and avoid awkward situations but also to allow time to prioritize and plan for the things you really want to act upon.

In order for this to work, you will first need to create an email address or obtain a dedicated P.O. Box specifically for this purpose. Then, whenever anyone asks for a financial favor, simply inform them that due to an overwhelming number of existing requests, your advisors have helped you devise a system that allows you to sort them in a more manageable way (technically, we are advising you right now, so this is already true). Provide the person with your dedicated P.O. Box or email address (you can even have this information printed onto business cards if you’d like), and inform them that everything sent there will be taken into consideration and prioritized appropriately. If someone already knows their request is unlikely to make the cut, this is often enough to shift the burden of guilt and avoid further discussion. But if you really want to drive the point home, consider mentioning the tax implications on gift-giving, or make note of your plans to work with your favorite charity. Likewise, if you happen to think of any additional people or situations that may warrant your financial assistance, you can always send these requests to yourself on their behalf.

Then, sometime after you’ve spoken with the proper advisor(s) and have developed a solid financial plan, evaluate the maximum amount you’d be willing to spend helping the people in your life while taking into consideration any charitable donations you might like to make as well. Finally, at pre-determined intervals, look through all the requests, and begin sorting them appropriately. Some will be immediately obvious; many will not. You may wish to create separate “yes,” “no,” and “maybe” piles. But keep in mind that this method is intended to be used over a long period of time and that today’s “maybes” may become tomorrow’s “yeses.” Furthermore, realize that today’s “yes” pile doesn’t necessarily need to be paid in full up front. With this in mind, be careful not to allot too much money to this system the first time through.

Also, consider creating your own standard policies that can be applied to financial requests. Maybe you want to make a rule that you will not be allocating any money within the first year of winning the lottery. Or perhaps you want it to be known that you will only help out each person once or that no request may exceed a certain dollar amount. But the most important thing to note is that if you choose to adopt this approach, you should adhere to it 100% of the time. When people know and understand your rules up front, there will be little room for resentment in the future. And although it may be a little uncomfortable to accept and follow these rules at the start, pretty soon you and everyone else will simply view them as “the way things are.”

Unless somebody was already counting on your financial assistance before you hit the jackpot, that person’s sense of entitlement should not change immediately after your win. But all too often, it does. And that is why it is so important to be judicious regarding the examples you set. The people who really care about you should be able to appreciate your position and respect your decision to set your own conditions. And if you decide to help them out financially, that will be entirely your own decision.