One of the most common questions we hear is whether the pros outweigh the cons to selling annuity payments. It is true that there are some cons to selling your annuity payments in certain situations. For one, you will be selling your annuity payments at a discount. The tradeoff, of course, is that you get a lump sum of cash to do with as you wish. So if you don’t need the money, you should probably hold off on selling your annuity payments. Second, if you are not good with money, it might not be a great idea to get a large sum of money as there’s a greater chance you will blow through it.