Once you know the reason you are investing your money, you need to do some research to discover whether or not your expectations are reasonable. If you are near retirement and have $500,000 in the bank, you aren't going to be able to turn that into a $200,000 annual income without taking some extraordinary risks that could wipe out your entire nest egg. More likely, you could add just shy of $1,700 per month to your family's coffers following the famous four percent rule.